116412-83-0

Basic information

• Product Name: 4-Chloro-3,4'-DimethoxyBenzophenone
• Synonyms: 4-CHLORO-(3,4-DIMETHOXY)-BENZOPHENONE 98+%;4-Chloro-3',4'-dimethoxybenzophenone
• CAS NO: 116412-83-0
• Molecular Formula: C₁₅H₁₃ClO₃
• Molecular Weight: 276.71
• EINECS: 404-610-1
• Product Categories: Naphthyridine,Quinoline
• Mol File: 116412-83-0.mol

Chemical Properties

• Melting Point: 111-112 °C(Solv: ethanol (64-17-5))
• Boiling Point: 414.5°Cat760mmHg
• Flash Point: 167.2°C
• Appearance: /
• Density: 1.216g/cm³
• Storage Temp.: 2-8°C
• Solubility: Chloroform; Dichloromethane; DMSO; Ethyl Acetate; Methanol
• CAS DataBase Reference: 4-Chloro-3,4'-DimethoxyBenzophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-3,4'-DimethoxyBenzophenone(116412-83-0)
• EPA Substance Registry System: 4-Chloro-3,4'-DimethoxyBenzophenone(116412-83-0)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61
• Hazardous Substances Data: 116412-83-0(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Industry:
4-Chloro-3,4'-DimethoxyBenzophenone is used as an intermediate in the synthesis of Dimethomorph-d8 (D460532), a labeled agricultural fungicide. It plays a crucial role in the development of effective fungicides to protect crops from fungal infections and ensure a stable food supply.
In the synthesis process, 4-Chloro-3,4'-DimethoxyBenzophenone acts as a key building block, enabling the production of the desired fungicidal compound. Its specific chemical structure allows for further reactions and modifications, ultimately leading to the formation of the active ingredient in the fungicide. This application highlights the importance of 4-Chloro-3,4'-DimethoxyBenzophenone in the agricultural sector, as it contributes to the development of innovative and effective solutions for crop protection.

Synthetic route

1,2-dimethoxybenzene (91-16-7) + 4-chloro-benzoyl chloride (122-01-0) → FeCl3 + 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0)

Conditions	Yield
	A n/a B 93%

1,2-dimethoxybenzene (91-16-7) + para-chlorobenzoic acid (74-11-3) → 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0)

Conditions	Yield
With boron trifluoride diethyl etherate at 80 - 90℃; for 0.05h; Microwave irradiation; chemoselective reaction;	89%

3,4-dimethoxy-benzaldehyde (120-14-9) + (4-chlorphenyl)magnesium bromide (873-77-8) → 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0)

Conditions	Yield
Stage #1: 3,4-dimethoxy-benzaldehyde; (4-chlorphenyl)magnesium bromide In tetrahydrofuran Stage #2: With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In dichloromethane	86%

1,2-dimethoxybenzene (91-16-7) + 4-chloro-benzoyl chloride (122-01-0) + 1,1,2,2-tetrachloroethane (79-34-5) → 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0)

Conditions	Yield
With FeCl3; graphite	84.3%
With FeCl3; graphite	84.3%
graphite	81.3%

1,2-dimethoxybenzene (91-16-7) + 4-chlorotrichloromethylbenzene (5216-25-1) + 1,1,2,2-tetrachloroethane (79-34-5) → 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0)

Conditions	Yield
graphite In water	79.5%

1,2-dimethoxybenzene (91-16-7) + 4-chloro-benzoyl chloride (122-01-0) → 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0)

Conditions	Yield
With Cl4Fe(1-)*C9H7N3O2*H(1+) In neat (no solvent) at 100℃; for 3h; Friedel-Crafts Acylation; Inert atmosphere;	70%
With aluminium trichloride In dichloromethane for 0.5h; Friedel-Crafts reaction;	53%
With aluminium trichloride In benzene at 55 - 60℃; for 2.5h; Friedel-Crafts reaction;

para-chlorobenzoic acid (74-11-3) → 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C / Reflux 2: aluminum (III) chloride / dichloromethane / 2 h / 0 °C / Reflux View Scheme

benzene-1,2-diol (120-80-9) → 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water / 1.33 h / 10 - 15 °C / Inert atmosphere; Large scale 1.2: 4.7 h / 20 - 50 °C / Inert atmosphere; Large scale 2.1: iron(III) chloride / hexane / 2.8 h / 120 °C / Inert atmosphere; Large scale View Scheme

1,2-dimethoxybenzene (91-16-7) + para-chloroacetophenone (99-91-2) → 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0)

Conditions	Yield
With iron(III) chloride In hexane at 120℃; for 2.8h; Temperature; Inert atmosphere; Large scale;

Methyltriphenylphosphonium bromide (1779-49-3) + 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → C16H15ClO2

Conditions	Yield
With sodium hydride	89%

4-acetylmorpholine (1696-20-4) + tert-Amyl alcohol (75-85-4) + sodium tert-pentoxide (14593-46-5) + 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → dimethomorph

Conditions	Yield
With carbon dioxide In 5,5-dimethyl-1,3-cyclohexadiene; di-isopropyl ether; paraffin oil	82.2%

ethylene glycol (107-21-1) + 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → 2-(4-chloro-phenyl)-2-(3,4-dimethoxy-phenyl)-[1,3]dioxolane (812685-05-5)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 40h; Heating;	82%

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → (4-chlorophenyl)-(4,5-dimethoxy-2-nitrophenyl)methanone (681469-99-8)

Conditions	Yield
With nitric acid; acetic acid at 0 - 20℃; for 0.5h;	77%
With nitric acid; acetic acid

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → 4-[3-(4-chlorophenyl)-5,6-dimethoxy-1H-2-indolyl]-2-butanone

Conditions	Yield
Multi-step reaction with 7 steps 1: 77 percent / HNO3; AcOH / 0.5 h / 0 - 20 °C 2: 67 percent / Fe; AcOH / H2O; ethyl acetate / 6 h / Heating 3: 78 percent / pyridine / 1 h / 20 °C 4: 86 percent / NaBH4 / ethanol / Heating 5: 76 percent / p-TsOH / CH2Cl2 / Heating 6: 81 percent / HCl / ethanol / Heating 7: 91 percent / KOH / methanol / 4 h / Heating View Scheme

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → 2-[4-chlorophenyl(hydroxy)methyl]-4,5-dimethoxy-1-(4-methylphenylsulfonamido)benzene (924635-48-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 77 percent / HNO3; AcOH / 0.5 h / 0 - 20 °C 2: 67 percent / Fe; AcOH / H2O; ethyl acetate / 6 h / Heating 3: 78 percent / pyridine / 1 h / 20 °C 4: 86 percent / NaBH4 / ethanol / Heating View Scheme

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → 2-(4-chlorobenzoyl)-4,5-dimethoxy-1-(4-methylphenylsufonamido)benzene (886493-87-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 77 percent / HNO3; AcOH / 0.5 h / 0 - 20 °C 2: 67 percent / Fe; AcOH / H2O; ethyl acetate / 6 h / Heating 3: 78 percent / pyridine / 1 h / 20 °C View Scheme

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → 4-methyl-N-{2-[(4-chlorophenyl)(5-methylfuran-2-yl)methyl]-4,5-dimethoxyphenyl}benzenesulfonamide (924635-54-1)

Conditions	Yield
Multi-step reaction with 5 steps 1: 77 percent / HNO3; AcOH / 0.5 h / 0 - 20 °C 2: 67 percent / Fe; AcOH / H2O; ethyl acetate / 6 h / Heating 3: 78 percent / pyridine / 1 h / 20 °C 4: 86 percent / NaBH4 / ethanol / Heating 5: 76 percent / p-TsOH / CH2Cl2 / Heating View Scheme

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → 4-[3-(4-chlorophenyl)-5,6-dimethoxy-1-(4-methylphenylsulfonyl)-1H-2-indolyl]-2-butanone (920457-61-0)

Conditions	Yield
Multi-step reaction with 6 steps 1: 77 percent / HNO3; AcOH / 0.5 h / 0 - 20 °C 2: 67 percent / Fe; AcOH / H2O; ethyl acetate / 6 h / Heating 3: 78 percent / pyridine / 1 h / 20 °C 4: 86 percent / NaBH4 / ethanol / Heating 5: 76 percent / p-TsOH / CH2Cl2 / Heating 6: 81 percent / HCl / ethanol / Heating View Scheme

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → (2-amino-4,5-dimethoxyphenyl)-(4-chlorophenyl)methanone (886494-44-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / HNO3; AcOH / 0.5 h / 0 - 20 °C 2: 67 percent / Fe; AcOH / H2O; ethyl acetate / 6 h / Heating View Scheme

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → 3-chloro-6-(3,4-dimethoxybenzoyl)benzoic acid

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 82 percent / p-toluenesulfonic acid / toluene / 40 h / Heating 2.1: butyllithium / hexane; tetrahydrofuran / 2 h / -20 °C 2.2: tetrahydrofuran; hexane / 3 h 3.1: 1.35 g / aq. hydrochloric acid / 4 h / Heating View Scheme

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → 5-chloro-2-[2-(3,4-dimethoxy-phenyl)-[1,3]dioxolan-2-yl]-benzenesulfonyl chloride

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 82 percent / p-toluenesulfonic acid / toluene / 40 h / Heating 2.1: butyllithium / hexane; tetrahydrofuran / 2 h / -20 °C 2.2: sulfur dioxide / tetrahydrofuran; hexane / 12 h / 20 °C 3.1: sulfuryl chloride / hexane / 0.5 h / 0 °C View Scheme

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → 5-chloro-2-[2-(3,4-dimethoxy-phenyl)-[1,3]dioxolan-2-yl]-benzoic acid (1027937-58-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 82 percent / p-toluenesulfonic acid / toluene / 40 h / Heating 2.1: butyllithium / hexane; tetrahydrofuran / 2 h / -20 °C 2.2: tetrahydrofuran; hexane / 3 h View Scheme

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → lithium; 5-chloro-2-[2-(3,4-dimethoxy-phenyl)-[1,3]dioxolan-2-yl]-benzenesulfinate

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 82 percent / p-toluenesulfonic acid / toluene / 40 h / Heating 2.1: butyllithium / hexane; tetrahydrofuran / 2 h / -20 °C 2.2: sulfur dioxide / tetrahydrofuran; hexane / 12 h / 20 °C View Scheme

4-acetylmorpholine (1696-20-4) + sodium tert-pentoxide (14593-46-5) + 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → dimethomorph

Conditions	Yield
In di-isopropyl ether; toluene

tert-butyl alcohol (75-65-0) + 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → dimethomorph

Conditions	Yield
In toluene; paraffin oil

4-acetylmorpholine (1696-20-4) + 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → dimethomorph

Conditions	Yield
With potassium hydroxide In tetrahydrofuran

4-acetylmorpholine (1696-20-4) + p-Tolylaceton (2096-86-8) + 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → 3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)-3-hydroxy-1-morpholinopropan-1-one + dimethomorph

Conditions	Yield
With potassium hydroxide In water; toluene

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → 4-chloro-3',4'-dimethoxydiphenylmethane (1239703-27-5)

Conditions	Yield
With aluminum (III) chloride; lithium aluminium tetrahydride for 2h; Reflux;

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → 4-chloro-3',4'-dihydroxydiphenylmethanone (134612-84-3)

Conditions	Yield
With boron tribromide In dichloromethane at -78 - 20℃; for 4h;

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → (3,4-dimethoxyphenyl)(4-chlorophenyl)methanone oxime (1385825-44-4)

Conditions	Yield
With hydroxylamine hydrochloride; sodium hydroxide In ethanol for 6h; Reflux;

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → isopropyl((2S)-1-(((3,4-dimethoxylphenyl)(4-chlorophenyl)methyl)amino)-3-methyl-1-oxobutan-2-yl)carbamate (1496524-38-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide; hydroxylamine hydrochloride / ethanol / 6 h / Reflux 2.1: ammonium hydroxide; zinc; ammonium acetate / ethanol / 1 h / Reflux 3.1: triethylamine; chloroformic acid ethyl ester / tetrahydrofuran / 1 h / 0 °C 3.2: 2 h / 20 °C View Scheme

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → (3,4-dimethoxyphenyl)(4-chlorophenyl)methylamine (1016697-21-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide; hydroxylamine hydrochloride / ethanol / 6 h / Reflux 2: ammonium hydroxide; zinc; ammonium acetate / ethanol / 1 h / Reflux View Scheme

Upstream product

• 91-16-7 1,2-dimethoxybenzene 
• 122-01-0 4-chloro-benzoyl chloride 
• 79-34-5 1,1,2,2-tetrachloroethane 
• 5216-25-1 4-chlorotrichloromethylbenzene 
• 74-11-3 para-chlorobenzoic acid 
• 120-80-9 benzene-1,2-diol 
• 99-91-2 para-chloroacetophenone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 93-07-2 Veratric acid 
• 155586-38-2 N,3,4-trimethoxy-N-methylbenzamide 
• 51833-36-4 4-chlorophenylmagnesium chloride 

Downstream Products

• 812685-05-5 2-(4-chloro-phenyl)-2-(3,4-dimethoxy-phenyl)-[1,3]dioxolane 
• 681469-99-8 (4-chlorophenyl)-(4,5-dimethoxy-2-nitrophenyl)methanone 
• 924635-48-3 2-[4-chlorophenyl(hydroxy)methyl]-4,5-dimethoxy-1-(4-methylphenylsulfonamido)benzene 
• 886493-87-4 2-(4-chlorobenzoyl)-4,5-dimethoxy-1-(4-methylphenylsufonamido)benzene 
• 924635-54-1 4-methyl-N-{2-[(4-chlorophenyl)(5-methylfuran-2-yl)methyl]-4,5-dimethoxyphenyl}benzenesulfonamide 
• 920457-61-0 4-[3-(4-chlorophenyl)-5,6-dimethoxy-1-(4-methylphenylsulfonyl)-1H-2-indolyl]-2-butanone 
• 886494-44-6 (2-amino-4,5-dimethoxyphenyl)-(4-chlorophenyl)methanone 
• 1027937-58-1 5-chloro-2-[2-(3,4-dimethoxy-phenyl)-[1,3]dioxolan-2-yl]-benzoic acid 
• 110488-70-5 dimethomorph 
• 1239703-27-5 4-chloro-3',4'-dimethoxydiphenylmethane 
• 134612-84-3 4-chloro-3',4'-dihydroxydiphenylmethanone 
• 1385825-44-4 (3,4-dimethoxyphenyl)(4-chlorophenyl)methanone oxime 
• 1496524-38-9 isopropyl((2S)-1-(((3,4-dimethoxylphenyl)(4-chlorophenyl)methyl)amino)-3-methyl-1-oxobutan-2-yl)carbamate 
• 1016697-21-4 (3,4-dimethoxyphenyl)(4-chlorophenyl)methylamine 

Relevant articles and documents

Gold-based immunochromatographic strip assay for detecting dimethomorph in vegetables

Dimethomorph (DMM) is a novel therapeutic fungicide, which is mainly used to control downy mildew, phytophthora, and other fungal diseases of grapes, leeks, and cucumbers. Its residue is harmful to the human body and the soil environment. In this study, the optimum monoclonal antibody (mAb) against DMM was prepared after routine fusion and selection. Based on the mAb, an indirect competitive enzyme-linked immunosorbent assay (ic-ELISA) and a gold nanoparticle immunochromatographic assay (GNP-ICA) were developed for detecting DMM in leek samples. The 50% inhibitory concentration (IC50) of the mAb was 1.823 ng mL-1, and its cross-reactivity with structurally related analogs was less than 3%. Under optimal conditions, the visible detection limit of this ICA method was 10 ng g-1, and the cutoff value of DMM in leeks was 100 ng g-1. The analysis of DMM in leeks showed that the results of the strip analysis were highly comparable with those of ic-ELISA and liquid chromatography-mass spectrometry LC-MS. Therefore, the GNP immunoassay is a sensitive screening method for detecting DMM residues in foods.

Tunable aryl imidazolium recyclable ionic liquid with dual br?nsted-lewis acid as green catalyst for friedel-crafts acylation and thioesterification

Unique tunable aryl imidazolium ionic liquids successfully catalyzed Friedel-Crafts acylation and thioesterification in sealed tubes. These reactions can form a C-C bond and a C-S bond with high atom economy. Ionic liquids exhibited high activity and catalyzed essential reactions with good to excellent yields while retaining their catalytic activities for recycling.

Arene Cyanation via Cation-Radical Accelerated-Nucleophilic Aromatic Substitution

Herein we describe a cation radical-accelerated-nucleophilic aromatic substitution (CRA-SNAr) of alkoxy arenes utilizing a highly oxidizing acridinium photoredox catalyst and acetone cyanohydrin, an inexpensive and commercially available cyanide source. This cyanation is selective for carbon-oxygen (C-O) bond functionalization and is applicable to a range of methoxyarenes and dimethoxyarenes. Furthermore, computational studies provide a model for predicting regioselectivity and chemoselectivity in competitive C-H and C-O cyanation of methoxyarene cation radicals.

Visible-Light-Enabled Oxidative Coupling of Alkenes with Dialkylformamides to Access Unsaturated Amides

A practical and direct method for oxidative cross-coupling of alkenes with dialkylformamides is established employing visible-light-enabled photoredox catalysis. This strategy allows efficient access to diverse unsaturated amides under mild reaction conditions. The application of an appropriate diaryliodonium salt was demonstrated to be critical to the success of this process. This catalyst system is well tolerant of a variety of useful functional groups.

Dimethomorph production method

The invention discloses a dimethomorph production method in the technical field of pesticide production. The production method comprises: 1) synthesizing veratrole; 2) synthesizing 3,4-dimethoxy-4-chloro-benzophenone; 3) synthesizing acetylmorpholine; and 4) synthesizing dimethomorph. Sodium tert-butoxide is taken as a basic catalyst for synthesizing dimethomorph from 3,4-dimethoxy-4-chloro-benzophenone and acetylmorpholine, and a sodium hydroxide solution is used to perform alkali washing on a reactant in a reaction vessel. Sodium hydroxide has a catalytic effect on synthesis of dimethomorphfrom 3,4-dimethoxy-4-chloro-benzophenone and acetylmorpholine. The defect that the catalytic effect of sodium tert-butoxide is gradually reduced due to unstable chemical property of sodium tert-butoxide and degradation of sodium tert-butoxide when sodium tert-butoxide comes into water is overcome. The dimethomorph product is improved in conversion rate and purity.

Selective acylation of phenols in boron trifluoride diethyl etherate solution and the mechanistic implication

In the presence of boron trifluoride diethyl etherate (BF3 · OEt2), direct acylation of phenols with free carboxylic acid is chemoselective and regioselective and no demethylation, if any, was observed. The para-directing effect of BF3·OEt2 is attributed to the large steric hindrance of the boron trifluoride-phenolic hydroxyl group complex, which blocks the ortho-acylation from occurrence. Microwave irradiation could not change the regioselectivity of BF3·OEt2 except the reaction time being greatly shortened.

Design, synthesis, and fungicidal activity of novel carboxylic acid amides represented by N-benzhydryl valinamode carbamates

Carboxylic acid amide (CAA) fungicides are an important class of agricultural fungicide with oomycete activity and low toxicity toward mammalian cells. To find CAA analogues with high activity against resistant pathogens, a series of substituted N-benzhydryl valinamide carbamate derivatives were designed and synthesized by introducing substituted aromatic rings into valinamide carbamate leads. Bioassays showed that some title compounds exhibited very good in vitro fungicidal activity against Phytophthora capsici and in vivo fungicidal activities against Pseudoperonospora cubensis. Topomer CoMFA was performed to explore the structure-activity relationship on the basis of the in vitro data. The dimethoxy substituted aromatic analogue 9e was found to display higher in vitro fungicidal activity against Phytophthora capsici than iprovalicarb but lower activity than mandipropamid, and higher in vivo fungicidal activity against Pseudoperonospora cubensis than dimethomorph at a dosage of 6.25 μg mL-1. This journal is the Partner Organisations 2014.

Synthesis and biological activity of halophenols as potent antioxidant and cytoprotective agents

A series of new bromophenols and chlorophenols were prepared by a practical route. The in vitro antioxidative activity of the halophenols was evaluated by the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging assay, and their cytoprotective activity was also tested on hydrogen peroxide (H2O2)-induced injury in human umbilical vein endothelial cells (HUVEC). All halophenols tested displayed moderate to good DPPH radical-scavenging activity, and two bromophenols, 2,3′-dibromo-4,5,6′-trihydroxydiphenylmethanone (16c) and 2,3-dibromo-4,5-dihydroxydiphenylmethanone (17c) exhibited high protective activity against H2O2-induced injury in HUVEC with EC50 values of 0.4 and 0.8 μM, respectively. The preliminary structure-activity relationships of these compounds were also investigated in order to determine the essential structures required for their bioactivities.

Simple route to 3-(2-indolyl)-1-propanones via a furan recyclization reaction

A simple route to 1-R-3-(2-indolyl)-1-propanones has been elaborated based on recyclization of 2-(2-aminobenzyl)furan derivatives. Being a modification of the Reissert indole synthesis, our approach employs the furan ring as a source of carbonyl function. This approach is general and allows varying of substituents in aromatic ring as well as in 3-position of indole nucleus.

Lithiation of 2-aryl-2-(chloroaryl)-1,3-dioxolanes and its application in the synthesis of new ortho-functionalized benzophenone derivatives

2-Aryl-2-(chloroaryl)-1,3-dioxolanes 4 were lithiated ortho to the ketal group of the chloroaryl ring by treatment with butyllithium in THF between -78 and 0°C. The site selectivity of some of the deprotonation reactions was rationalized by the long-range effect of the 4-chloro substituent. The lithio species thus generated were treated with various electrophiles to give ortho-functionalized benzophenone derivatives. Intramolecular competition between the aryl rings was observed in the lithiation of 2-(4-chlorophenyl)-2- (4-fluorophenyl)-1,3-dioxolane (4s). Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.