cas 5111-65-9, 2-Bromo-6-methoxynaphthalene

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A practical synthesis of 2-bromo-6-methoxynaphthalene
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Xu, Wei-Ming,He, Hong-Qiang
p. 107 - 109
(2010)
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Synthesis of functionalized molecular motors
Synthetic routes to two molecular motors are reported. The sterically hindered central olefinic bond connecting the two halves of these C 2-symmetric molecules was prepared by a McMurry reaction. In this way, a motor with two five-membered rings and a motor with two six-membered rings were prepared, both with two versatile methoxy substituents at positions not interfering with the rotary behavior. Georg Thieme Verlag Stuttgart.
Ter Wiel, Matthijs K. J.,Feringa, Ben L.
p. 1789 - 1796
(2005)
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The intramolecular Schmidt reaction of azides with tertiary alcohols: Synthesis of 5-(α-naphthyl)- and 5-(β-naphthyl)indolizidines as potential dopamine analogs and non-opiate antinociceptive agents
Intramolecular Schmidt reaction of the azido alcohols 9, 11, and 12 afforded the 5-naphthylindolizidines 10, 13, and 14, respectively. The naphthylmethylamine subunit present in each has an amine and a π-system oriented in a fashion similar to the β-phenethylamine subunit of dopamine and many of its agonists and antagonists. These analogs also closely resemble the bicyclic tertiary amines 8, which have recently been found to exhibit non-opiate analgesic activity. Testing of 10, 13, and 14 for dopaminergic activity is described.
Pearson, William H.,Gallagher, Brian M.
p. 12039 - 12048
(1996)
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Discovery of new and highly effective quadruple FFA1 and PPARα/γ/δ agonists as potential anti-fatty liver agents
Non-alcoholic fatty liver disease (NAFLD) has become the most common hepatic disease, while no drug was approved until now. The previous study reported that the quadruple FFA1/PPAR-α/γ/δ agonist RLA8 provided better efficacy than obeticholic acid on NASH. In the present study, two design strategies were introduced to explore better quadruple FFA1/PPAR-α/γ/δ agonists with improved metabolic stability. These efforts ultimately resulted in the identification of ZLY18, a quadruple FFA1/PPAR-α/γ/δ agonist with twice higher metabolic half-life than RLA8 in the liver microsome. In the triton-1339W-induced hyperlipidemic model, ZLY18 reversed hyperlipidemia to an almost normal level, which exhibited far stronger lipid-lowering effects than that of RLA8. Moreover, ZLY18 significantly decreased steatosis, hepatocellular ballooning, inflammation and liver fibrosis in NASH model even better than RLA8. Further mechanism studies suggested that ZLY18 exerts stronger effects than RLA8 on the regulation of the gene related to lipid synthesis, oxidative stress, inflammation and fibrosis. In addition, ZLY18 is more effective than pirfenidone in the prevention of CCl4-induced liver fibrosis. Besides, ZLY18 has an acceptable safety profile in the acute toxicity study at a high dose of 500 mg/kg. Therefore, ZLY18 represents a novel and highly promising quadruple FFA1/PPAR-α/γ/δ agonist worth of further investigation and development.
Cai, Zongyu,Deng, Liming,Geng, Xinqian,Hu, Lijun,Jiao, Shixuan,Li, Zheng,Ren, Qiang,Wang, Bin,Yang, Ying,Zhang, Luyong,Zhou, Zongtao
supporting information

(2021/12/27)

Hydrogen-Bond-Donor Solvents Enable Catalyst-Free (Radio)-Halogenation and Deuteration of Organoborons
A hydrogen bond donor solvent assisted (radio)halogenation and deuteration of organoborons has been developed. The reactions exhibited high functional group tolerance and needed only an ambient atmosphere. Most importantly, compared to literature methods, our conditions are more consistent with the principals of green chemistry (e.g., metal-free, strong oxidant-free, more straightforward conditions).
Yang, Yi,Gao, Xinyan,Zeng, Xiaojun,Han, Junbin,Xu, Bo
supporting information
p. 1297 - 1300
(2020/12/23)

Preparation method of nitrogen-alkyl (deuterated alkyl) aromatic heterocycle and alkyl (deuterated alkyl) aryl ether compound
The invention provides a method for preparing nitrogen-alkyl(deuterated alkyl)aromatic heterocycle and alkyl(deuterated alkyl)aryl ether compounds. The method adopted in the invention specifically comprises the following steps: firstly, adding an alkoxy base (MOR') or a combination reagent Q (comprising a base M'X, an alcohol C and a molecular sieve E) into a solvent B to be stirred; then, addingan aromatic compound D of nitrogen sulfonyl or oxygen sulfonyl into a mixture; separating and purifying after reaction to obtain nitrogen-alkyl(deuterated alkyl)aromatic heterocycle or alkyl(deuterated alkyl)aryl ether. The method can realize one-step conversion from an electron withdrawing benzenesulfonyl protecting group on a nitrogen or oxygen atom to an electron donating alkyl protecting group, avoids using highly toxic alkyl halide, and has advantages of being efficient, economical, environmentally friendly, mild in condition, good in substrate universality and high in yield; the prepareddeuterated compounds can be widely applied to the fields of pharmaceutical chemistry and organic chemistry synthesis.
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Paragraph 0093-0097

(2021/04/03)

Gold(i)-catalyzed Nicholas reaction with aromatic molecules utilizing a bifunctional propargyl dicobalt hexacarbonyl complex
A benchtop-stable reagent for the catalytic Nicholas reaction was developed. By combining a propargyl dicobalt hexacarbonyl cluster with an ortho-alkynylbenzoate unit and a fluorous tag, introduction of a propargyl hexacarbonyl complex on various aromatic compounds having acid- or base-sensitive functional groups becomes possible by using a gold(i) catalyst. In addition, the presence of a fluorous tag facilitates convenient separation of the target products from byproducts.
Okamura, Toshitaka,Fujiki, Shogo,Iwabuchi, Yoshiharu,Kanoh, Naoki
supporting information
p. 8522 - 8526
(2019/10/02)

Detosylative (Deutero)alkylation of Indoles and Phenols with (Deutero)alkoxides
An efficient strategy for N/O-(deutero)alkylation of indoles and phenols with alkoxides/alcohols as the alkylation reagents is described. The consecutive detosylation/alkylation transformations feature mild reaction conditions, high ipso-selectivity, and good functional group tolerance (>50 examples). A one-pot selective N-alkylation of unprotected indoles with alcohols and TsCl is also realized. The application of this method is demonstrated by the introduction of isotope-labeled (CD3 and 13CH3) groups using the readily accessible labeled alcohols and the synthesis of pharmaceuticals.
Zhu, Ming-Hui,Yu, Cheng-Long,Feng, Ya-Lan,Usman, Muhammad,Zhong, Dayou,Wang, Xin,Nesnas, Nasri,Liu, Wen-Bo
supporting information
p. 7073 - 7077
(2019/09/30)

Nickel-Catalyzed Amination of Silyloxyarenes through C–O Bond Activation
Silyloxyarenes were utilized as electrophilic coupling partners with amines in the synthesis of aniline derivatives. A diverse range of amine substrates were used, including cyclic or acyclic secondary amines, secondary anilines, and sterically hindered primary anilines. Additionally, a range of sterically hindered and unhindered primary aliphatic amines were employed, which have previously been challenging with other classes of aryl ether electrophiles. Orthogonal couplings of silyloxyarenes with aryl methyl ethers are illustrated, where selectivity between the two C?O electrophiles is determined by ligand control, thereby allowing complementary and selective late-stage diversification of either electrophile. Finally, a sequential coupling displays the utility of this amination method along with the reversal in intrinsic reactivity between aryl methyl ethers and silyloxyarenes.
Wiensch, Eric M.,Montgomery, John
supporting information
p. 11045 - 11049
(2018/07/31)

A conjugated system of curcumin analogs increase and its preparation method and application
The invention discloses a curcumin analogue with an enlarged conjugated system and a preparation method and application thereof. The structural feature of the curcumin analogue is shown in the general formula (I), wherein R1 is hydrogen and methoxyl, R2 is hydrogen, hydroxy and methoxyl, and two naphthalene nucleuses are connected through a 1,6-heptadiene-3,5-diketone joining chain. The naphthol is used as a raw material, the naphthalene nucleus curcumin analogue with the superior activity for hepatoma carcinoma cell HepG2 cell proliferation is synthesized, and the activity of the curcumin analogue is superior to that of natural curcumin. The curcumin analogue with the enlarged conjugated system has the great significance in guiding discovery of prodrugs and designing lead compounds.
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Paragraph 0104; 0105; 0106

(2017/08/25)

By using micro-channel modular reaction device to prepare 2-bromo-6- methoxy naphthalene method
The invention discloses a method for preparing 2-bromine-6-methoxynaphthalene with a micro-channel modularized reaction device. The method comprises the following steps: 2-methoxynaphthalene and glacial acetic acid are mixed uniformly, and bromine and the mixture of 2-methoxynaphthalene and the glacial acetic acid are respectively pumped into the first microstructure reactor of the micro-channel modularized reaction device and are kept for 5-10 min at 40-60 DEG C, wherein the molar ratio of 2-methoxynaphthalene to bromine is 1 to (1.5-4); the material discharged from the first microstructure reactor is injected into a second microstructure reactor filled with powdered iron, and is kept for 4-8 min at 65-95 DEG C, the material discharged from the second microstructure reactor is guided into ice water to separate out a great amount of solid, suction filtration and water washing are performed, a filter cake is dissolved with chloroform, washed with 10wt% of a NaOH water solution to be neutral, dried with anhydrous sodium sulfate, and evaporated to remove chloroform, and the residues are recrystallized with anhydrous ethyl alcohol to obtain white needle crystals.
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Paragraph 0028; 0029

(2017/01/05)

PESTICIDE COMPOUNDS
The present invention relates to novel compounds of the formula I and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof wherein C1 is C or CH; C2 is C or CH; A1 is N or C; A2 is N, C(R2), N(R3), O, S or C(R4,R5); and A3 is N, O, S, N(R6), C(R7) or C(R8,R9); where one or two non-adjacent bonds in the 5-membered ring formed by C1, C2, A1, A2 and A3 are double bonds, while the others are single bonds, provided that the bond between A1 and A2 or the bond between A1 and C1 or the bond between A2 and A3 or the bond between C1 and C2 or the bond between A3 and C2 is a double bond further provided that at least one of A1, A2 and A3 is N, N(R3) or N(R6), and where Ar, R1, R2, R3, R4,R5, R6, R7, R8, R9 and (R)k are as defined in the claims and in the description, which are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.
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Page/Page column 281; 282

(2015/02/02)

Time-dependent solid-state polymorphism of a series of donor-acceptor dyads
In order to exploit the use of favorable electrostatic interactions between aromatic units in directing the assembly of donor-acceptor (D-A) dyads, the present work examines the ability of conjugated aromatic D-A dyads with symmetric side chains to exhibit solid-state polymorphism as a function of time during the solid formation process. Four such dyads were synthesized, and their packing in the solid state from either slower (10-20 days) or faster (1-2 days) evaporation from solvent was investigated using single crystal X-ray analysis and powder X-ray diffraction. Two of the dyads exhibited tail-to-tail (A-A) packing upon slower evaporation from solvent and head-to-tail (D-A) packing upon faster evaporation from solvent. A combination of single-crystal analysis and XRD patterns were used to create models, wherein a packing model for the other two dyads is proposed. Our findings suggest that while side chain interactions in asymmetric aromatic dyads can play an important role in enforcing segregated D-A dyad assembly, slowly evaporating symmetrically substituted aromatic dyads allows for favorable electrostatic interactions between the aromatic moieties to facilitate the organization of the dyads in the solid state.
Peebles, Cameron,Alvey, Paul M.,Lynch, Vincent,Iverson, Brent L.
supporting information
p. 290 - 299
(2014/01/17)

Decarbonylative halogenation by a vanadium complex
Metal-catalyzed halogenation of the C-H bond and decarbonylation of aldehyde are conventionally done in nature. However, metal-mediated decarbonylative halogenation is unknown. We have developed the first metal-mediated decarbonylative halogenation reaction starting from the divanadium oxoperoxo complex K3V5+2(O 22-)4(O2-)2(μ-OH) (1). A concerted decarbonylative halogenation reaction was proposed based on experimental observations.
Rana, Sujoy,Haque, Rameezul,Santosh, Ganji,Maiti, Debabrata
p. 2927 - 2932
(2013/04/24)

Method for Obtaining Novel Derivatives of Naphthalene for the In Vivo Diagnosis of Alzheimer's Disease
This invention relates to a chemistry branch, particularly to the field of compounds' organic synthesis that belongs to the aromatic bicyclic or naphthalene category, used in the detection of amyloid sheets. These new naphthalene derivatives have a general formula: Wherein R represents mutually independent groups. In I: R1:-alkylenyl-C(O)NH-alkylenyl-R3, -alkylenyl-C(O)O—R4, R3:—COOH, —OH, —SH, —NH2, -alkyl-NH-alkyl-N-dithiocarbamate alkaline earth metal salts, R4: H, succinimidyl group, R2: —H,-alkyl. In II: R1: -alkyl, -alkylenyl-halide-alkylenyl-hydroxyl-alkylenyl-O-aryl, —O-alkylsulfonate alkylenyl, R2: -halide-alkylenyl-O-aryl, -alkylenyl-O-alkylsulfonate, -alkylenyl-halide-, —CH(O), —HC═C(CN)2, —HC═CHNO2, -alkylenyl-NH2, -alkylenyl-NH-alkyl, -alkylenyl-alkyl-N-dithiocarbamate alkaline salts. The terms “alkyl” and “alkylenyl” refer to linear or branched aliphatic chains, preferably from 1 to 4 carbon atoms and the term halide to fluorine, bromine or iodine. These compounds are neutral, lipophilic and have low molecular weight and therefore they cross the blood brain barrier and attach to the amyloid sheets. The present invention provides procedures for obtaining naphthalene derivatives with good yields, which can be practical, economical and adapted to a larger-scale manufacturing. We are unaware whether the compounds presented in this invention have been previously reported.
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(2013/02/27)

Design of an extremely high birefringence nematic liquid crystal based on a dinaphthyl-diacetylene mesogen
We designed dinaphthyl-diacetylene-based nematic liquid crystals with alkoxy tails (DNDA-OCm) and evaluated their birefringence (Δn). Actual measurements of pure target compounds showed that DNDA-OC2 had the highest value of 0.62 at 550 nm at Tc + 10 °C.
Arakawa, Yuki,Nakajima, Shunpei,Kang, Sungmin,Shigeta, Masayuki,Konishi, Gen-Ichi,Watanabe, Junji
supporting information; experimental part
p. 13908 - 13910
(2012/08/08)

METHOD FOR OBTAINING NOVEL DERIVATIVES OF NAPHTALENE FOR THE IN VIVO DIAGNOSIS OF ALZHEIMER 'S DISEASE
This invention relates to a chemistry branch, particularly to the field of compounds' organic synthesis that belongs to the aromatic bicyclic or naphthalene category, used in the detection of amyloid sheets. These new naphthalene derivatives have a general formula: Where R represents mutually independent groups. In I: R1: -alkylenyl-C(O)NH-alkylenyl-R3, -alkylenyl-C(O)O-R4; R3: -COOH, -OH, - SH, -NH2, -alkyl-NH, -alkyl-N-dithiocarbamate alkaline earth metal salts. R4: succinimidyl group. R2: -H, -alkyl. The term "alkyl" is characterized by a linear or branched aliphatic chain, hydrogen and saturated carbon atoms, comprising a methyl, ethyl, n-propyl, iso-propyl, n-butyl or iso-butyl groups. The term "alkylenyl" refers to a divalent analog of a linear or branched alkyl group, preferably ethylenyl (CH2CH2) or butylenyl (CH2CH2CH2CH2) radicals. In II: R1: -alkyl, and R2 is -alkylenyl-O-arylsulfonate, -alkylenyl-halide, -CH(O), alkylenyl-NH2, -alkylenyl-NH-alkyl, -alkylenyl-alkyl-N-dithiocarbamate salts such as cesium, potassium or sodium. The term "alkyl" is characterized by a linear or branched aliphatic chain, hydrogen and saturated carbon atoms, preferably methyl, ethyl, n-propyl, iso-propyl, n-butyl or iso-butyl. The term "alkylenyl" refers to a divalent analog of a linear or branched alkyl group, preferably propylenyl (-CH2CH2 CH2) radical. The term halide refers to fluorine, bromine or iodine. or, In II: R1: -alkylenyl-halide, -alkylenyl-O-arylsulfonate and R2: -halide, -alkylenyl-O-arylsulfonate, -alkylenyl-O-alkylsulfonate, -alkylenyl-halide, -CH(O), -HC=C(CN)2, - HC=CHNO2, -alkylenyl-NH2, -alkylenyl-NH-alkyl, -alkylenyl-alkyl-N-dithiocarbamate salts such as cesium, potassium or sodium. The term "alkylenyl" refers to a divalent analog of a linear or branched alkyl group, preferably propylenyl (-CH2CH2 CH2) radical. The term halide refers to fluorine, bromine or iodine. These compounds are neutral, lipophilic and have low molecular weight and therefore they cross the blood brain barrier and attach to the amyloid sheets. The present invention provides procedures for obtaining naphthalene derivatives with good yields, which can be practical, economical and adapted to a larger-scale manufacturing. We are unaware whether the compounds presented in this invention have been previously reported.
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Paragraph 0057

(2013/03/26)

Synthesis of aryl alkyl ethers by alkylation of phenols with quaternary ammonium salts
Phenolic compounds can be efficiently O-methylated with tetramethylammonium chloride in diglyme or polyethyleneglycol (PEG) at temperatures of 150-160 °C and in the presence of either K2CO3 or NaOH. When applying benzyl-trimethylammonium chloride as a reagent, the benzylation and methylation of phenols occurs, with the benzylation product always predominating. With allyl-substituted phenols as substrates and using NaOH as a base it was possible to achieve both the alkylation and the double-bond isomerization of the allyl group to obtain (E/Z)-propenyl-substituted methyl and benzyl aryl ethers in a single preparative step.
Maras, Nenad,Polanc, Slovenko,Kocevar, Marijan
experimental part
p. 29 - 36
(2010/09/05)

Naphthylisopropylamine and N-benzylamphetamine derivatives as monoamine oxidase inhibitors
A series of naphthylisopropylamine and N-benzyl-4-methylthioamphetamine derivatives were evaluated as monoamine oxidase inhibitors. Their potencies were compared with those of a series of amphetamine derivatives, to test if the increase of electron richness of the aromatic ring and overall size of the molecule might improve their potency as enzyme inhibitors. Molecular dockings were performed to gain insight regarding the binding mode of these inhibitors and rationalize their different potencies. In the case of naphthylisopropylamine derivatives, the increased electron-donating capacity and size of the aromatic moiety resulting from replacement of the phenyl ring of amphetamine derivatives by a naphthalene system resulted in more potent compounds. In the other case, extension of the arylisopropylamine molecule by N-benzylation of the amino group led to a decrease in potency as monoamine oxidase inhibitors.
Vilches-Herrera, Marcelo,Miranda-Sepulveda, Juan,Rebolledo-Fuentes, Marco,Fierro, Angelica,Luehr, Susan,Iturriaga-Vasquez, Patricio,Cassels, Bruce K.,Reyes-Parada, Miguel
experimental part
p. 2452 - 2460
(2009/09/08)

Amplification of the cotton effect of a single chromophore through liposomal ordering-stereochemical assignment of plakinic acids I and J
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Dalisay, Doralyn S.,Quach, Timy,Nicholas, Gillian N.,Molinski, Tadeusz F.
supporting information; experimental part
p. 4367 - 4371
(2009/10/23)

Microwave-assisted methylation of phenols with tetramethylammonium chloride in the presence of K2CO3 or Cs2CO3
We have evaluated the potential of using tetramethylammonium chloride (Me4NCl) as an alternative methylating agent for phenols under microwave-assisted conditions. Its chemical behavior was tested in a reaction with 2-naphthol in the presence of various bases and solvents. The method was then applied in 1,2-dimethoxyethane or toluene under heterogeneous conditions for the O-methylation of a series of phenolic compounds. We found that many simple phenols can be methylated in the presence of K2CO3, whereas some other less-reactive phenols require the presence of the more reactive Cs2CO3.
Mara?, Nenad,Polanc, Slovenko,Ko?evar, Marijan
experimental part
p. 11618 - 11624
(2009/04/05)

Methylation of arenes via Ni-catalyzed aryl C-O/F activation
Aryl C-O and C-F can be transformed into C-Me via Ni-catalyzed coupling with MeMgBr under mild conditions. The Royal Society of Chemistry.
Guan, Bing-Tao,Xiang, Shi-Kai,Wu, Tao,Sun, Zuo-Peng,Wang, Bi-Qin,Zhao, Ke-Qing,Shi, Zhang-Jie
p. 1437 - 1439
(2008/12/21)

NOVEL ORGANIC SEMICONDUCTOR COMPOUND, AND ORGANIC THIN FILM TRANSISTOR USING THE SAME
The present invention relates to novel mono- molecular organic semiconductor compounds and organic thin film transistors comprising the same. The organic semiconductor compounds according to the present invention are characterized by a structure of an acene derivative substituted with acetylene groups at both ends, a structure of anthracene derivative substituted with acetylene groups, or a structure of a multi-nuclear aromatic derivative functionalized by naphthalene having an electron-donor substituent at both ends.
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Page/Page column 47

(2008/12/04)

Site directed nuclear bromination of aromatic compounds by an electrochemical method
Direct bromination of a wide range of aromatic compounds possessing electron-donating groups, such as methoxy, hydroxy or amino groups, have been carried out by two-phase electrolysis. This electrochemical method results in high yields (70-98%) of monobromo compounds and usually with high regioselectivity (>95%) for the para position.
Raju,Kulangiappar,Anbu Kulandainathan,Uma,Malini,Muthukumaran
p. 4581 - 4584
(2007/10/03)

Solid state S-methylation of thiols and O-methylation of phenols and naphthols with dimethyl sulfate under microwave irradiation
Mild and efficient S-methylation of thiols and o-methylation of phenols and naphthals occurs with dimethyl sulfate (DMS) supported on basic alumina under microwave irradiation in solventless system. Copyright Taylor & Francis Inc.
Heravi, Majid M.,Ahari, Neda Zamani,Oskooie, Hossein A.,Ghassemzadeh, Mitra
p. 1701 - 1712
(2007/10/03)

Process research and structural studies on nabumetone
A short, simple and economical process for large-scale preparation of nabumetone has been developed. The single-crystal structures of nabumetone and one of its key intermediates have been determined by X-ray diffraction studies. Two impurities have been isolated and characterised.
Prabhakar,Reddy, C. Bakki,Reddy, Ch. Maheedhara,Nageshwar,Devi, A. Sivalakshmi,Babu, J. Moses,Vyas,Sarma,Reddy
p. 121 - 125
(2013/09/08)

Production of nabumetone or precursors thereof
In producing nabumetone or precursor thereof, use is made of 2-bromo-6-methoxynaphthalene formed by (a) methylating 6-bromo-2-naphthol with methyl bromide or methyl chloride, in a halogen-free liquid solvent comprising at least about 40% by weight of one or more compounds of the formula RZ where R is a hydrogen atom or an alkyl group, and Z is a hydroxyl group or a cyanide group with the proviso that if Z is a cyanide group, R is an alkyl group, and in the presence of at least one strong base; and (b) recovering and purifying 2-bromo-6-methoxynaphthalene so formed. The 6-bromo-2-naphthol in turn is preferably formed by reacting 1,6-dibromo-2-naphthol with hydrogen in a halogen-containing liquid solvent comprising at least about 50% by weight of (A) at least one liquid organic halide solvent in which the halogen content has an atomic number of 35 or less or (B) a mixture of water and at least one such liquid organic halide solvent, and in the presence of catalytic amounts of (i) a tungsten carbide-based catalyst, and (ii) at least one phase transfer catalyst, most preferably while purging HBr from the reaction mixture as it is formed. In this way, the quantities of by-products formed in the overall operation are reduced, the need for use of excess iron and/or dimethyl sulfate as reaction components is avoided, and the overall efficiency of plant operation is improved especially when conducted on a large scale.
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(2008/06/13)

Production of racemic 2-(6-methoxy-2-naphthyl) propionic acid of precursors thereof
In producing (±)-2-(6-methoxy-2-naphthyl)propionic acid or precursor thereof from 2-bromo-6-methoxynaphthalene, use is made of 2-bromo-6-methoxynaphthalene formed by (a) methylating 6-bromo-2-naphthol with methyl chloride in a solvent comprising one or more compounds, RZ, where R is a hydrogen atom or an alkyl group, and Z is --OH or --CN provided that if Z is --CN, R is alkyl, and in the presence of a strong base; and (b) recovering and purifying 2-bromo-6-methoxynaphthalene so formed. Preferably, the 6-bromo-2-naphthol is formed by (1) reacting 1,6-dibromo-2-naphthol with hydrogen, in a solvent comprising (a) organic halide in which the halogen has an atomic number of 35 or less or (b) a mixture of water and such organic halide, and in the presence of catalytically effective amounts of (i) a tungsten carbide-based catalyst, and (ii) phase transfer catalyst; and (2) separating 6-bromo-2-naphthol from the organic halide solvent so that the 6-bromo-2-naphthol is substantially free of halogen-containing impurities before use in the above methylation reaction. This technology makes possible reductions in quantities of co-products formed, eliminates need for use of excess iron and/or dimethyl sulfate as reaction components, and makes possible improvements in plant operating efficiency. Precursors of (±)-2-(6-methoxy-2-naphthyl)propionic acid formed from such 2-bromo-6-methoxynaphthalene are Grignard reagent of 2-bromo-6-methoxynaphthalene, bis(6-methoxy-2-naphthyl)zinc, 6-methoxy-2-naphthylzinc halide, 6-methoxy-2-naphthyllithium, 6-methoxy-2-naphthylcopper(I), bis(6-methoxy-2-naphthyl)cadmium, 6-methoxy-2-naphthylcadmium halide, and 6-methoxy-2-vinylnaphthalene.
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(2008/06/13)

Convenient routes to 2-aryl-2-fluoropropionic acids: Synthesis of monofluorinated analogues of (±)-ibuprofen, (±)-naproxen and related compounds
The synthesis of α-fluorinated arylpropionic acids 5 as analogues of the nonsteroidal anti-inflammatory agents (NSAIDs) flurbiprofen 1, ibuprofen 3 and naproxen 4 is accomplished by the oxidation of the corresponding primary alcohols 9. The latter are accessible on two different pathways showing their general applicability by variation of the aromatic moiety. Furthermore the influence of the fluorine substituent towards the conformation of the acid moiety in the crystal lattice is shown by comparative X-ray studies of compound 5c.
Goj, Olav,Kotila, Sirpa,Haufe, Guenter
p. 12761 - 12774
(2007/10/03)

Synthesis of Novel Non-centrosymmetric Crystalline Materials for Quadratic Non-linear Optics
Racemic 6,6'-bis-(phenylethynyl)-1,1'-binaphthyls and five of the six 6,4'-disubstituted 2-naphthylphenylacetylenes designed and synthesized show non-linear optical (NLO) activity in the Kurtz and Perry second-harmonic generation (SHG) powder test.
Wong, Man Shing,Nicoud, Jean-Francois
p. 249 - 250
(2007/10/02)

LDA (lithium diisopropylamide) mediated reactions of 1-naphthalynes with lithiated acetonitriles and 1,4-dipolar nucleophilic anions
3-Bromo-2-methoxy-(5) and 3-bromo-2-methoxy-6-methylnaphthalene (6) yield 1-naphthalyne intermediates which react with various α-lithiated nitriles 10 to afford both rearranged 1-arylmethyl- or 1-hetarylmethyl-3-methoxynaphthalene-2-carbonitriles 11 and 12, respectively, and α-naphthylated aryl- or hetarylacetonitriles 13 and 14, respectively. Product distributions 11:13 favoring rearranged nitriles (65:35-90:10) were obtained from LDA-mediated reactions of 5 with arylacetonitriles 9a, b and thiopheneacetonitriles 9c, d. Similar treatment of 6 with 9a-d gave product distributions 12:14 heavily in favor of rearranged nitriles (> 90:10) presumably due to the ability of the additional 7-methyl group to increase the rate of cyclization of the initial aryne-nitrile anion adduct, the crucial step in the rearrangement pathway. However treatment of either 5 or 6 with α-lithiated pyridylacetonitriles 9e, f or 2-benzimidazolylacetonitrile (9g) gave product distributions 11:13 or 12:14, respectively, heavily in favor of α-naphthylated acetonitriles (30:7010:90). Additionally, several precursors to methoxy-substituted 1-naphthalynes 5, 19 and 20 were found to undergo cycloaddition with the dipolar nucleophilic precursors 3-cyanophthalide (17) and α-cyano-o-tolunitrile (21) to give angularly substituted benz[a]anthracene derivatives 18, 22.
Biehl,Rakeeb Deshmukh,Dutt
p. 885 - 888
(2007/10/02)

Naphthyl Dioxetane Phosphates: Synthesis of Novel Substrates for Enzymatic Chemoluminescent Assays
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Edwards, B.,Sparks, A.,Voyta, J. C.,Strong, R.,Murphy, O.,Bronstein, I.
p. 6225 - 6229
(2007/10/02)

Hydroxamic acid inhibitors of 5-lipoxygenase
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Summers,Mazdiyasni,Holms,Ratajczyk,Dyer,Carter
p. 574 - 580
(2007/10/02)

Synthese und fluessigkristalline Eigenschaften 2,6-disubstituierter Naphtaline
The syntheses and the mesomorphic properties of a series of novel 2,6-disubstituted naphthalenes are described. 4-benzonitriles 5 and 4-benzonitriles 8 exhibit wide-range nematic mesophases. 6,6'-Di(n-Alkyl)-2,2'-binaphthyls 6 have been isolated as by-products from the reaction mixtures of 5.Some of these novel compounds have polymorphic properties.The esters 13 and 15 of 4-(6-hydroxy-2-naphthyl)benzonitrile show enhanced mesophase stabilities which reach maximum values in the series of α,β-unsaturated esters 15.The 4-(n-pentyl)benzoate 14 of the same (hydroxynaphthyl)benzonitrile has a melting point of 125 deg and a clearing point of > 310 deg.This particular derivative belongs to those liquid-crystalline compounds having the broadest purely nematic-phase range.In addition, (RS)-4-(2-pentyl-6-chromanyl)benzonitrile (20) and three compounds with two and four laterally arranged CN groups at the bicyclooctene, bicyclooctadiene, and phenyl-ring systems 31-33 were synthesized.Only 20 shows mesomorphic properties.
Lauk, Urs H.,Skrabal, Peter,Zollinger, Heinrich
p. 1406 - 1426
(2007/10/02)

Process for the manufacture of 2-alkoxy-6-bromo-naphthalenes
A new process, which can be carried out on the technical scale, had been found for the preparation of 2-alkoxy-6-bromo-naphthalenes, especially suitable as starting compounds for the synthesis of estrogens, which comprises brominating 2-hydroxy-naphthalene-1-carboxylic acid with bromine, decarboxylating the 6-bromo-2-hydroxynaphthalene-1-carboxylic acid by heating the reaction mixture at 100 - 125° C, and alkylating the 6-bromo-2-hydroxy-naphthalene formed. The process can be conducted easily and with high yields.
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(2008/06/13)