766-51-8

Basic information

• Product Name: 2-Chloroanisole
• Synonyms: 1-chloro-2-methoxy-benzen;2-chloromethoxybenzene;2-Chlorophenol methyl ether;Anisole, o-chloro-;anisole,o-chloro-;benzene,1-chloro-2-methoxy-;o-Chloromethoxybenzene;o-Chlorophenyl methyl ether
• CAS NO: 766-51-8
• Molecular Formula: C₇H₇ClO
• Molecular Weight: 142.58
• EINECS: 212-167-9
• Product Categories: Aromatic Ethers;Anisole;Anisoles, Alkyloxy Compounds & Phenylacetates;Chlorine Compounds;Ethers;Organic Building Blocks;Oxygen Compounds;Building Blocks;C2 to C7;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 766-51-8.mol
• Article Data: 116

Chemical Properties

• Melting Point: -26.8°C
• Boiling Point: 195-196 °C(lit.)
• Flash Point: 169 °F
• Appearance: Clear light yellow/Liquid
• Density: 1.123 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.506mmHg at 25°C
• Refractive Index: n20/D 1.545(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: 0.49g/L(25 oC)
• BRN: 2042179
• CAS DataBase Reference: 2-Chloroanisole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloroanisole(766-51-8)
• EPA Substance Registry System: 2-Chloroanisole(766-51-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 766-51-8(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR LIGHT YELLOW LIQUID

Uses

2-Chloroanisole was used in headspace solid-phase microextraction method for the determination of haloanisoles in wine and spirit samples.

Synthesis Reference(s)

Journal of the American Chemical Society, 96, p. 2252, 1974 DOI: 10.1021/ja00814a045The Journal of Organic Chemistry, 41, p. 732, 1976 DOI: 10.1021/jo00866a043

General Description

2-Chloroanisole undergoes acetylation with acetic anhydride over large pore zeolites to give 4-acetyl-2-chloroanisole.

InChI:InChI=1/C7H7ClO/c1-9-7-5-3-2-4-6(7)8/h2-5H,1H3

Synthetic route

2-Methoxyphenylboronic acid (5720-06-9) → 2-Chloroanisole (766-51-8)

Conditions	Yield
With N-chloro-succinimide; copper(l) chloride In acetonitrile at 80℃; for 18h;	97%
With N-chloro-succinimide In acetonitrile at 80℃; for 24h;	90%

2-monochlorophenol (95-57-8) + dimethyl sulfate (77-78-1) → 2-Chloroanisole (766-51-8)

Conditions	Yield
Stage #1: 2-monochlorophenol With potassium carbonate In acetone for 0.25h; Stage #2: dimethyl sulfate In acetone for 10h; Reflux;	96%
With sodium hydroxide In water at 90℃; for 0.5h;	84.6%
With potassium hydroxide at 100℃;
With sodium hydroxide at 100℃;
With lithium hydroxide In tetrahydrofuran for 1h; Ambient temperature; Yield given;

methoxybenzene (100-66-3) → 4-chloromethoxybenzene (623-12-1) + 2-Chloroanisole (766-51-8)

Conditions	Yield
With lithium chloride In N,N-dimethyl acetamide at 30℃; Pt anode, graphite cathode, sintered glass diaphragm, 1.3 V vs. SCE, 965 C;	A 95.8% B 2.8%
With aluminum oxide; sodium chlorite; water; manganese(III) acetylacetonate In dichloromethane at 25℃; for 0.583333h; Product distribution; other solvents, inorganic support materials, times and temperatures, also without H2O;	A 85% B 8%
With chlorine; natural kaolinitic clay In tetrachloromethane for 2h; Heating;	A 85% B 9%

2-monochlorophenol (95-57-8) + methyl iodide (74-88-4) → 2-Chloroanisole (766-51-8)

Conditions	Yield
With sodium carbonate In dichloromethane at 20℃;	95%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;	51%
With sodium hydroxide In N,N-dimethyl acetamide at 25℃; Rate constant;
With potassium carbonate at 130℃;

2-bromoanisole (578-57-4) → 2-Chloroanisole (766-51-8)

Conditions	Yield
With nickel dichloride In N,N-dimethyl-formamide at 170℃; for 0.0833333h; microwave irradiation;	94%
With CuCl-alumina In various solvent(s) at 150℃; for 24h;	54 % Chromat.
With hydrogenchloride; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; oxygen In water; acetonitrile at 25℃; for 1.5h; Irradiation;	53 %Chromat.

3-chloro-4-methoxybenzyl alcohol (14503-45-8) → 2-Chloroanisole (766-51-8)

Conditions	Yield
With chlorobis(cyclooctene)-iridium(I) dimer; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; lithium chloride In water; 1,3,5-trimethyl-benzene at 170℃; for 18h; Schlenk technique; Inert atmosphere;	91%

2-monochlorophenol (95-57-8) + carbonic acid dimethyl ester (616-38-6) → 2-Chloroanisole (766-51-8)

Conditions	Yield
With layered double hydroxide - supported L-methionine at 180℃; for 6h; Autoclave; chemoselective reaction;	90%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 0.0583333h; microwave irradiation;	85%
With dimanganese decacarbonyl at 180℃; for 1h;	2%
With leucine intercalated Mg-Al layered double hydorxide at 180℃; for 6h; Autoclave; Green chemistry; chemoselective reaction;	86 %Chromat.

N-chloro-N-(4-methylphenyl)acetamide (14596-60-2) + methoxybenzene (100-66-3) → 4-chloromethoxybenzene (623-12-1) + 2-Chloroanisole (766-51-8) + N-(2-chloro-4-methylphenyl)acetamide (18931-78-7) + 4-Methylacetanilide (103-89-9)

Conditions	Yield
at 110℃; for 12h; Mechanism; Orton Haloaniline Rearrangement; Inert atmosphere; Darkness;	A 82% B n/a C n/a D 87%

Methyl trichloroacetate (598-99-2) + 2-monochlorophenol (95-57-8) → 2-Chloroanisole (766-51-8)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate at 150℃; for 2h;	85%

2-methoxy-benzenediazonium; tetrachloro cuprate(II) → 2-Chloroanisole (766-51-8)

Conditions	Yield
In dimethyl sulfoxide Ambient temperature;	84%

carbon dioxide (124-38-9) + 2,3-dichloroanisole (1984-59-4) → 1-chloro-3-methoxy-benzene (2845-89-8) + 2-Chloroanisole (766-51-8) + 2-chloro-6-methoxybenzoic acid (3260-89-7) + 2-chloro-3-methoxybenzoic acid (33234-36-5)

Conditions	Yield
With tetrabutylammomium bromide In N,N-dimethyl-formamide at 5℃; electrolysis (I=0.4 A); Yields of byproduct given;	A n/a B n/a C n/a D 78%
With tetrabutylammomium bromide In N,N-dimethyl-formamide at 5℃; electrolysis (I=0.4 A); Yields of byproduct given;	A n/a B n/a C 78% D n/a

2-monochlorophenol (95-57-8) + phosphorous acid trimethyl ester (121-45-9) → 2-Chloroanisole (766-51-8)

Conditions	Yield
With boron trifluoride In diethyl ether for 0.0416667h; microwave irradiation;	76%

2-methoxy-phenol (90-05-1) → 2-Chloroanisole (766-51-8)

Conditions	Yield
With P,P-dichlorophenylphosphine oxide; phosphorus pentachloride at 160℃; for 5h;	73.3%
With phosphorus pentachloride Destillation des Produktes mit Wasserdampf;

2-Methoxyphenylboronic acid (5720-06-9) → 2-Chloroanisole (766-51-8) + 5-chloro-2-methoxyphenyl boronic acid (89694-48-4)

Conditions	Yield
With 1,3-dichloro-5,5-dimethylhydantoin; sodium methylate In methanol; water; acetonitrile at 60℃;	A 18 % Chromat. B 67%
With 1,3-dichloro-5,5-dimethylhydantoin In water; acetonitrile at 60℃;	A 11% B 84 % Chromat.

2-Nitroanisole (91-23-6) → 2-Chloroanisole (766-51-8)

Conditions	Yield
With Dichlorophenylphosphine In various solvent(s) at 170℃; for 5h;	66%

2-methoxybenzenediazonium o-benzenedisulfonamide → 2-Chloroanisole (766-51-8)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; copper In acetonitrile at 20℃; for 0.75h; Substitution;	62%

methoxybenzene (100-66-3) → 4-chloromethoxybenzene (623-12-1) + 1,3-dichloro-4-methoxybenzene (553-82-2) + 2-Chloroanisole (766-51-8)

Conditions	Yield
With hydrogenchloride; 3-methyl-1-(butyl-4-sulfonyl)imidazolium nitrate In water at 80℃; for 21h; Green chemistry;	A 24% B 60% C 9%
With N-chloro-succinimide; xenon difluoride at 25℃;	A 46% B 2% C 7%
With benzyl(trimethyl)ammonium tetrachloroiodate In acetic acid at 70℃; for 24h; Product distribution; different substrates, ratios of BTMA ICl4, solvent, reaction times and temperatures;

2-monochlorophenol (95-57-8) + tetramethlyammonium chloride (75-57-0) → 2-Chloroanisole (766-51-8)

Conditions	Yield
With potassium carbonate In 1,2-dimethoxyethane at 145℃; for 1h; Microwave irradiation; Inert atmosphere; Sealed vessel;	55%

3-chloro-4-methoxyphenylboronic acid (175883-60-0) → 2-Chloroanisole (766-51-8)

Conditions	Yield
With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); water In toluene at 90℃; for 1h; Microwave irradiation; Green chemistry;	47%

2-methoxy-phenylamine (90-04-0) → 1-fluoro-2-methoxybenzene (321-28-8) + 2-Chloroanisole (766-51-8)

Conditions	Yield
With hydrogen fluoride; ammonium chloride; copper(l) chloride; sodium nitrite Product distribution; a.) 20 deg C, 1 h, 2.) irradiation, 20 deg C, 6 h;	A 43% B 20%

2-methoxy-phenylamine (90-04-0) → 2-Chloroanisole (766-51-8)

Conditions	Yield
With tert.-butylnitrite; N-benzyl-N,N,N-triethylammonium chloride; copper dichloride; 10-camphorsulfonic acid In acetonitrile at 20℃; for 24h; Time; Solvent;	33%

1,2-dichlorotetramethylsilane (4342-61-4) + 2-Methoxybenzoyl chloride (21615-34-9) → 2-Chloroanisole (766-51-8) + chloro(2-methoxyphenyl)dimethylsilane (60458-00-6)

Conditions	Yield
bis(benzonitrile)palladium(II) dichloride; triphenylphosphine at 145℃; for 15h;	A 18% B 32%

methanol (67-56-1) + sodium 4-chlorophenolate (1193-00-6) → 2-Chloroanisole (766-51-8)

Conditions	Yield
With carbon monoxide at 180℃;

2-Nitroanisole (91-23-6) → 2-Chloroanisole (766-51-8) + 2,4,6-Trichlorophenol (88-06-2)

Conditions	Yield
With thionyl chloride at 180 - 200℃;

2-monochlorophenol (95-57-8) → 2-Chloroanisole (766-51-8)

Conditions	Yield
With sodium hydroxide; methyl p-toluene sulfonate
With sodium hydroxide; dimethyl sulfate In sulfuric acid; water	195 grams (91.5%)

methanol (67-56-1) + 1-chloro-2-fluorobenzene (348-51-6) → 2-Chloroanisole (766-51-8)

Conditions	Yield
<(η-C6H6)(η-C5EtMe4)Rh>(2+)*2 In nitromethane at 80℃; for 96h;	19 % Chromat.
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 2,2,2-trifluoroethanol; 1,2-dichloro-ethane at 40℃; for 48h; Irradiation;

2,6-dichloroanisole (1984-65-2) → 2-Chloroanisole (766-51-8) + methoxybenzene (100-66-3)

Conditions	Yield
With tetrabutylammonium perchlorate In N,N-dimethyl-formamide at 25 - 30℃; Title compound not separated from byproducts;	A 7 % Chromat. B 39 % Chromat.

2,4,6-trichloroanisole (87-40-1) → 4-chloromethoxybenzene (623-12-1) + 1,3-dichloro-4-methoxybenzene (553-82-2) + 2-Chloroanisole (766-51-8) + 2,6-dichloroanisole (1984-65-2)

Conditions	Yield
With (C2H5)3NH2CO2; palladium on activated charcoal In acetonitrile at 80℃; Yield given. Further byproducts given. Yields of byproduct given;

2,4,6-trichloroanisole (87-40-1) → 4-chloromethoxybenzene (623-12-1) + 1,3-dichloro-4-methoxybenzene (553-82-2) + 2-Chloroanisole (766-51-8) + methoxybenzene (100-66-3)

Conditions	Yield
With tetrabutylammonium perchlorate In N,N-dimethyl-formamide at 25 - 30℃; Title compound not separated from byproducts;	A 34 % Chromat. B 2 % Chromat. C n/a D 41 % Chromat.
With tetrabutylammonium perchlorate In N,N-dimethyl-formamide at 25 - 30℃; Product distribution; other chlorinated aromatic ethers;	A 34 % Chromat. B 2 % Chromat. C 1 % Chromat. D 41 % Chromat.

sodium acetate (127-09-3) + methoxybenzene (100-66-3) → 4-chloromethoxybenzene (623-12-1) + 2-methoxyphenyl acetate (613-70-7) + 4-methoxyphenyl acetate (1200-06-2) + 2-Chloroanisole (766-51-8)

Conditions	Yield
With tungsten(VI) chloride; acetic acid In dichloromethane Ambient temperature; Title compound not separated from byproducts;	A 4 % Chromat. B 13 % Chromat. C 25 % Chromat. D 5 % Chromat.

2-Chloroanisole (766-51-8) → 4-bromo-2-chloro-1-methoxybenzene (50638-47-6)

Conditions	Yield
With (CH3)4Br In liquid sulphur dioxide at -23℃; Rate constant;	100%
With (CH3)4Br In liquid sulphur dioxide at -23℃;	100%
With N-Bromosuccinimide; iodine In acetonitrile for 12h; Darkness;	99%

2-Chloroanisole (766-51-8) + acetyl chloride (75-36-5) → 4-acetyl-2-chloroanisole (37612-52-5)

Conditions	Yield
With aluminium trichloride In dichloromethane at 0℃; for 2h;	100%
With nitrogen; aluminium trichloride In chloroform	76%
With aluminum (III) chloride In chloroform at 0 - 20℃; for 17.42h;	76%
With aluminium trichloride for 4h; heating;	52%
With aluminium trichloride

2-Chloroanisole (766-51-8) + phenylboronic acid (98-80-6) → 2-methoxy-1,1'-biphenyl (86-26-0)

Conditions	Yield
With potassium phosphate; N,N-diisopropyl 2-dicyclohexylphosphino-4-phenylbenzamide; tris(dibenzylideneacetone)dipalladium (0) In toluene at 110℃; for 1.33333h; Suzuki cross-coupling reaction;	100%
With (3-phenylallyl)(chloro)-[1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene]palladium(II); triethylamine In water at 50℃; for 6h; Suzuki-Miyaura reaction; Inert atmosphere; Micellar solution;	100%
With C34H41Cl2N3OPd; potassium tert-butylate In water; isopropyl alcohol at 80℃; for 15h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;	99%

2-Chloroanisole (766-51-8) + benzaldehyde (100-52-7) → 2-methoxyphenyl(phenyl)methanol (22788-49-4)

Conditions	Yield
Stage #1: 2-Chloroanisole With iodine; magnesium In tetrahydrofuran at 150℃; for 1h; Inert atmosphere; Microwave irradiation; Stage #2: benzaldehyde In tetrahydrofuran at 100℃; for 0.5h; Microwave irradiation;	100%
Stage #1: 2-Chloroanisole With iodine; magnesium In tetrahydrofuran at 150℃; for 1h; microwave irradiation; Stage #2: benzaldehyde In tetrahydrofuran at 100℃; for 0.5h; Grignard reaction; microwave irradiation;	99%

2-Chloroanisole (766-51-8) + (4bS,5R,9bS,10R)-4b,5,9b,10-Tetrahydro-indeno[2,1-a]indene-5,10-diol → C30H24Cl2O2

Conditions	Yield
With iron(III) chloride at 50℃; for 18h; Inert atmosphere; regioselective reaction;	100%

2-Chloroanisole (766-51-8) + p-toluidine (106-49-0) → N-benzyl-2-methoxyaniline (50798-94-2)

Conditions	Yield
With johnphos; sodium t-butanolate; palladium diacetate In toluene at 20℃; for 14h; Arylation;	99%

2-Chloroanisole (766-51-8) + benzylamine (100-46-9) → N-benzyl-2-methoxyaniline (50798-94-2)

Conditions	Yield
With johnphos; sodium t-butanolate; palladium diacetate In toluene at 20℃; for 14h; Substitution; Amination;	99%
With [Pd(2-aminobiphenyl)(PCyp2ArXyl2)](OMs); sodium t-butanolate In 1,4-dioxane at 100℃; for 19h; Inert atmosphere; Schlenk technique;	99%
With 2,6-di-tert-butyl-4-methyl-phenol; [1,3-bis(2,6-diisopentylphenyl)-4,5-dichloroimidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride; sodium hydride In toluene at 60℃; for 16h; Inert atmosphere; Schlenk technique;	98%

2-Chloroanisole (766-51-8) + 2-Methylphenylboronic acid (16419-60-6) → 2-methoxy-2'-methyl-1,1'-biphenyl (19853-12-4)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium fluoride; C58H47P In tetrahydrofuran for 13h; Suzuki-Miyaura coupling; Inert atmosphere; Reflux;	99%
With potassium phosphate; C28H31ClN2Ni; triphenylphosphine In tert-Amyl alcohol; toluene at 110℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube;	98%
With potassium tert-butylate; C61H90Cl4N6Pd2 In ethanol at 27℃; for 0.5h; Suzuki-Miyaura Coupling; Sealed tube;	98%

2-Chloroanisole (766-51-8) → N,N-bis(2-methoxyphenyl)amine (7287-75-4)

Conditions	Yield
With lithium amide; tris(dibenzylideneacetone)dipalladium (0); johnphos; sodium t-butanolate In toluene at 80℃; for 19h;	99%

2-Chloroanisole (766-51-8) + bis(pinacol)diborane (73183-34-3) → pinacol 2-anisylboronate (190788-60-4)

Conditions	Yield
With sodium acetate; bis(dibenzylideneacetone)-palladium(0); XPhos for 12h; Miyaura Borylation Reaction; Heating;	99%
With potassium 2,2,2-trifluoroethoxide; dichlorobis(trimethylphosphine)nickel In tetrahydrofuran at 100℃; for 12h; Inert atmosphere; Sealed tube;	76%
With potassium acetate; bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine In 1,4-dioxane at 80℃; for 48h;	70 % Chromat.

2-Chloroanisole (766-51-8) + diphenylamine (122-39-4) → N-(2-methoxyphenyl)diphenylamine (20441-01-4)

Conditions	Yield
With palladium diacetate; sodium t-butanolate; ruphos In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Green chemistry;	99%
With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 100℃; for 5h;	95%

2-Chloroanisole (766-51-8) + acetophenone (98-86-2) → 2-(2-methoxyphenyl)-1-phenylethan-1-one (27356-33-8)

Conditions	Yield
With C41H50ClN3Pd; sodium t-butanolate In 1,4-dioxane at 100℃; for 4h;	99%
With C41H46Cl2FeN4Pd; potassium tert-butylate In 1,4-dioxane at 100℃; for 3h; Inert atmosphere;	95%
With N-heterocyclic carbene-palladacycle; sodium t-butanolate In tetrahydrofuran at 70℃; for 3h;	85%

2-Chloroanisole (766-51-8) + 1-phenyl-propan-1-one (93-55-0) → 2-(2-methoxy-phenyl)-1-phenyl-propan-1-one

Conditions	Yield
With C40H44ClN3Pd; sodium t-butanolate In toluene at 80℃; for 3h; Inert atmosphere;	99%
With N-heterocyclic carbene-palladacycle; sodium t-butanolate In tetrahydrofuran at 70℃; for 3h;	98%
With sodium t-butanolate; (N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)Pd(OAc)2 In 1,4-dioxane at 60℃; for 1h;	94%

morpholine (110-91-8) + 2-Chloroanisole (766-51-8) → N-(2-methoxyphenyl)morpholine (27347-13-3)

Conditions	Yield
With 5-(di-tert-butylphosphino)-1′, 3′, 5′-triphenyl-1′H-[1,4′]bipyrazole; potassium hydroxide; tris(dibenzylideneacetone)dipalladium (0) In tert-Amyl alcohol; water at 90℃; for 5h;	99%
With (1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)Pd(cinnamyl, 3-phenylallyl)Cl; sodium t-butanolate In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Inert atmosphere; Green chemistry;	99%
With C28H29Cl2N3OPd; potassium tert-butylate In toluene at 110℃; for 15h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	99%

2-Chloroanisole (766-51-8) + 2,6-dimethylaniline (87-62-7) → N-(2,6-dimethylphenyl)-2-methoxyaniline (58656-24-9)

Conditions	Yield
With 5-(di-tert-butylphosphino)-1′, 3′, 5′-triphenyl-1′H-[1,4′]bipyrazole; potassium hydroxide; tris(dibenzylideneacetone)dipalladium (0) In tert-Amyl alcohol; water at 90℃; for 5h;	99%
With potassium tert-butylate In 1,4-dioxane at 110℃; for 3h;	99%
Stage #1: 2-Chloroanisole With PdCl(cinnamyl)(N,N′-bis(2,6-bis(diphenylmethyl)-4-methylphenyl)imidazol-2-ylidene); potassium 2-methylbutan-2-olate In neat (no solvent) at 25℃; for 0.0833333h; Buchwald-Hartwig Coupling; Stage #2: 2,6-dimethylaniline In neat (no solvent) at 25℃; for 24h; Buchwald-Hartwig Coupling;	94%

2-Chloroanisole (766-51-8) + cyclohexylamine (108-91-8) → N-(cyclohexylamino)-o-anisidine

Conditions	Yield
With (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl di-t-butylphosphine; sodium t-butanolate; palladium diacetate In 1,2-dimethoxyethane at 100℃; for 36h;	99%
With C63H54Cl3N3OPd; potassium 2-methylbutan-2-olate In 1,4-dioxane at 100℃; for 2h; Buchwald-Hartwig Coupling;	92%
With potassium tert-butylate In 1,4-dioxane at 110℃; for 3h;	72%

2-Chloroanisole (766-51-8) + rac-methylbenzylamine (618-36-0) → N-(2-methoxy-phenyl)-1-phenyl-ethylamine

Conditions	Yield
With 5-(di-tert-butylphosphino)-1′, 3′, 5′-triphenyl-1′H-[1,4′]bipyrazole; potassium hydroxide; tris(dibenzylideneacetone)dipalladium (0) In tert-Amyl alcohol; water at 90℃; for 5h;	99%

2-Chloroanisole (766-51-8) + aniline (62-53-3) → 2-methoxy-N-phenylaniline (1207-92-7)

Conditions	Yield
With potassium tert-butylate In 1,4-dioxane at 110℃; for 3h;	99%
With C16H34ClPPd; sodium t-butanolate In toluene at 100℃; Buchwald-Hartwig amination; Inert atmosphere;	96%
With (1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)Pd(cinnamyl, 3-phenylallyl)Cl; sodium t-butanolate In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Inert atmosphere; Green chemistry;	95%

2-Chloroanisole (766-51-8) + 2,5-Dimethylaniline (95-78-3) → N-(2-methoxyphenyl)-2,5-dimethylaniline

Conditions	Yield
With potassium tert-butylate In 1,4-dioxane at 110℃; for 3h;	99%
With (SIPr)PdCl2(TEA); potassium tert-butylate In 1,2-dimethoxyethane at 50℃; for 4.5h; Buchwald-Hartwig cross coupling; Inert atmosphere;	92%
With C37H44ClN2O3PPd; potassium hydroxide; tert-butyl alcohol In water at 100℃; for 12h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	90%

2-Chloroanisole (766-51-8) + N-methylaniline (100-61-8) → (2-methoxyphenyl)methylphenylamine

Conditions	Yield
With palladium diacetate; sodium t-butanolate; ruphos In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Green chemistry;	99%
With C16H34ClPPd; sodium t-butanolate In toluene at 100℃; Buchwald-Hartwig amination; Inert atmosphere;	97%
With C37H44ClN2O3PPd; potassium hydroxide; tert-butyl alcohol In water at 100℃; for 12h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	92%

para-bromotoluene (106-38-7) + 2-Chloroanisole (766-51-8) → 2-methoxy-4'-methylbiphenyl (92495-53-9)

Conditions	Yield
Stage #1: para-bromotoluene With lithium Stage #2: With zinc(II) chloride Stage #3: 2-Chloroanisole; nickel phosphine amido pincer complex In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 70℃; for 12h; Negishi cross-coupling; Further stages.;	99%

ortho-tolylmagnesium bromide (932-31-0) + 2-Chloroanisole (766-51-8) → 2-methoxy-2'-methyl-1,1'-biphenyl (19853-12-4)

Conditions	Yield
With iron(II) triflate; sodium t-butanolate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In tetrahydrofuran at 60℃; for 16h; Glovebox; Sealed tube; Inert atmosphere;	99%
Stage #1: 2-Chloroanisole With Ni(PPh3)(1,3-di-tert-butylimidazol-2-ylidene)Br2 In tetrahydrofuran at 0℃; for 0.0333333h; Inert atmosphere; Schlenk technique; Stage #2: ortho-tolylmagnesium bromide In tetrahydrofuran at 60℃; for 4h; Inert atmosphere; Schlenk technique;	98%
With C46H55ClFeN3Pd; lithium chloride In tetrahydrofuran at 60℃; for 24h; Kumada coupling reaction; Inert atmosphere;	95%

acetamide (60-35-5) + 2-Chloroanisole (766-51-8) → 2-methoxyacetanilide (93-26-5)

Conditions	Yield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In tert-butyl alcohol at 110℃; for 7h;	99%
With potassium phosphate; t-BuBrettPhos; water; palladium diacetate In tert-butyl alcohol at 110℃; for 3h; Inert atmosphere;	91%

2-Chloroanisole (766-51-8) + 2-Methoxyphenylboronic acid (5720-06-9) → 2,2'-Dimethoxybiphenyl (4877-93-4)

Conditions	Yield
With potassium phosphate; C50H63Cl2N3Pd In ethanol at 80℃; for 4h; Suzuki-Miyaura Coupling;	99%
Stage #1: 2-Methoxyphenylboronic acid With potassium phosphate; N,N-diisopropyl 2-dicyclohexylphosphino-5-(3'-nitrophenyl)benzamide; palladium diacetate In tetrahydrofuran at 23℃; for 0.0166667h; Suzuki-Miyaura cross-coupling; Inert atmosphere; Stage #2: 2-Chloroanisole In tetrahydrofuran at 23℃; for 36h; Suzuki-Miyaura cross-coupling; Inert atmosphere;	78%
With palladium diacetate; caesium carbonate; P-phenyl-2,2,6,6-tetramethyl-phosphorinan-4-ol In toluene at 110℃; for 48h; Suzuki-Miyaura cross coupling; Inert atmosphere;	70%

tert-butyl carbamate (4248-19-5) + 2-Chloroanisole (766-51-8) → tert-butyl 2-methoxyphenylcarbamate (154150-18-2)

Conditions	Yield
With 4-diphenylphosphino-13-dicyclohexylphosphino-[2.2]paracyclophane; water; palladium diacetate; caesium carbonate In 1,4-dioxane at 125℃; for 24h; Buchwald-Hartwig coupling;	99%
With di-tert-butyl{2′-isopropoxy-[1,1′-binaphthalen]-2-yl}phosphane; caesium carbonate; bis(dibenzylideneacetone)-palladium(0) In tert-butyl alcohol at 100℃; for 20h; Inert atmosphere;	40%
With palladium diacetate; caesium carbonate; XPhos In 1,4-dioxane at 100℃; for 24h;	10 %Chromat.

2-Chloroanisole (766-51-8) + cyclopropylboronic acid (411235-57-9) → 1-cyclopropyl-2-methoxybenzene (10292-66-7)

Conditions	Yield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); rac-3-(tert-butyl)-4-(2,6-dimethoxyphenyl)-2,3-dihydrobenzo[d][1,3]oxaphosphole In toluene at 100℃; for 24h; Suzuki coupling; Inert atmosphere;	99%

2-Fluoroaniline (348-54-9) + 2-Chloroanisole (766-51-8) → 2-fluoro-N-(2-methoxyphenyl)aniline (1514859-18-7)

Conditions	Yield
With Pd-PEPPSI-(2,6-(3-pentyl)pentylphenyl-2H-imidazol-2-ylidene)Cl-o-picoline; caesium carbonate In 1,2-dimethoxyethane at 24℃; for 24h; Buchwald-Hartwig Coupling; Inert atmosphere; Glovebox;	99%
With [IPr*·H][Pd(η3-cin)Cl2]; potassium tert-butylate at 60 - 80℃; for 2h; Buchwald-Hartwig Coupling; Sealed tube;	80%

2-methyl-9H-fluorene (1430-97-3) + 2-Chloroanisole (766-51-8) → C21H18O

Conditions	Yield
With NHC-Pd(II)-Im; potassium tert-butylate In 1,4-dioxane at 120℃; for 12h; Inert atmosphere; Schlenk technique;	99%

2-Chloroanisole (766-51-8) + phenylpropyolic acid (637-44-5) → 2-phenylethynylanisole (41398-67-8)

Conditions	Yield
With bis[dicyclohexyl(2,4,6-triisopropyl-[1,1':3',1''-terphenyl]-2-yl)phosphane]palladium(II) dichloride; caesium carbonate In tetrahydrofuran at 80℃; for 1.5h; Temperature; Solvent; Reagent/catalyst;	99%
With (R)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; palladium diacetate; caesium carbonate In dimethyl sulfoxide at 130℃; for 12h;	33%

2-Chloroanisole (766-51-8) + benzoyl chloride (98-88-4) → (3-chloro-4-methoxyphenyl)(phenyl)methanone (10547-61-2)

Conditions	Yield
With copper(II) ferrite In 1,2-dichloro-ethane at 35 - 38℃; for 18h; Friedel-Crafts Acylation;	98%
With aluminum (III) chloride In dichloromethane at 0℃; for 3h; Inert atmosphere;	82%
With aluminium trichloride	81%
With aluminium trichloride; 1,1,2,2-tetrachloroethane at 120 - 130℃;
With carbon disulfide; aluminium trichloride at 0℃;

Upstream product

• 100-66-3 methoxybenzene 
• 95-57-8 2-monochlorophenol 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 348-51-6 1-chloro-2-fluorobenzene 
• 578-57-4 2-bromoanisole 
• 54135-80-7 1,2,3-trichloro-4-methoxybenzene 
• 14503-45-8 3-chloro-4-methoxybenzyl alcohol 
• 14596-60-2 N-chloro-N-(4-methylphenyl)acetamide 
• 108-90-7 chlorobenzene 
• 1984-59-4 2,3-dichloroanisole 
• 1984-58-3 2,5-dichloroanisole 
• 90-05-1 2-methoxy-phenol 
• 1193-00-6 sodium 4-chlorophenolate 

Downstream Products

• 107776-23-8 2-ethyl-4-(3-chloro-4-methoxy-phenyl)-4-oxo-butyric acid 
• 13719-57-8 3-chloro-4-methoxybenzyl chloride 
• 23446-86-8 bis-(3-chloro-4-methoxy-phenyl)-methane 
• 4903-09-7 3-chloro-4-methoxy-benzaldehyde 
• 89978-93-8 3-chloro-4-methoxy-benzoic acid amide 
• 74697-33-9 3-chloro-4',4-dimethoxybenzophenone 
• 37612-52-5 4-acetyl-2-chloroanisole 
• 105475-81-8 4-(3-chloro-4-methoxy-phenyl)-2-methyl-4-oxo-butyric acid 
• 99407-76-8 tris(2-methoxyphenyl)methanol 
• 71354-31-9 5-(3-Chloro-4-methoxy-phenyl)-5-oxo-pentanoic acid 
• 99414-56-9 5-(3-Chloro-4-methoxy-phenyl)-3-methyl-5-oxo-pentanoic acid 
• 89818-36-0 3-chloro-4-methoxyphenylisothiocyanate 
• 70154-90-4 ethyl (3-chloro-4-methoxyphenyl)glyoxylate 
• 250686-92-1 1-(3-chloro-4-methoxyphenyl)heptan-1-one 

Relevant articles and documents

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Oxidative Photochlorination of Electron-Rich Arenes via in situ Bromination

Electron-rich arenes are oxidatively photochlorinated in the presence of catalytic amounts of bromide ions, visible light, and 4CzIPN as organic photoredox catalyst. The substrates are brominated in situ in a first photoredox-catalyzed oxidation step, followed by a photocatalyzed ipso-chlorination, yielding the target compounds in high ortho/para regioselectivity. Dioxygen serves as a green and convenient terminal oxidant. The use of aqueous hydrochloric acid as the chloride source reduces the amount of saline by-products.

Dehydroxyalkylative halogenation of C(aryl)-C bonds of aryl alcohols

We herein report Cu mediated side-directed dehydroxyalkylative halogenation of aryl alcohols. C(aryl)-C bonds of aryl alcohols were effectively cleaved, affording the corresponding aryl chlorides, bromides and iodides in excellent yields. Aryl alcohols could serve as both aromatic electrophilic and radical synthetic equivalents during the reaction.