121872-94-4

Usage

Uses

Used in Pharmaceutical Industry:
2'-Chloro-4',5'-difluoroacetophenone is used as an intermediate in the production of various drugs. Its unique chemical structure allows for the synthesis of a wide range of pharmaceutical compounds, contributing to the development of new medications.
Used in Agrochemical Industry:
In the agrochemical industry, 2'-Chloro-4',5'-difluoroacetophenone serves as an intermediate in the synthesis of various pesticides. Its properties enable the creation of effective pest control agents, helping to protect crops and ensure food security.
Used in Organic Synthesis:
2'-Chloro-4',5'-difluoroacetophenone is utilized in organic synthesis as a versatile reagent. Its chemical properties allow for the formation of various organic compounds, expanding the scope of chemical reactions and contributing to the advancement of organic chemistry.
Used as a Reagent in Chemical Reactions:
As a reagent, 2'-Chloro-4',5'-difluoroacetophenone plays a crucial role in facilitating specific chemical reactions. Its presence can enhance the efficiency and selectivity of these reactions, making it an essential component in the field of chemical research and development.

Synthetic route

4-chloro-1,2-difluorobenzene (696-02-6) + acetyl chloride (75-36-5) → 2'-chloro-4',5'-difluoroacetophenone (121872-94-4)

Conditions	Yield
aluminium trichloride	82%
With aluminium trichloride Acylation;	80%
With aluminium trichloride at 60℃; for 9h;	75%

2-fluoro-5-chloronitrobenzene (345-18-6) → 2'-chloro-4',5'-difluoroacetophenone (121872-94-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: H2 / 5 percent Pt/C / 1,2-dimethoxy-ethane / 24 h / 2585.74 Torr 2: BF3*Et2O; t-BuONO / 1,2-dimethoxy-ethane / 1 h / -5 °C 3: 49 percent / 0.5 h / 170 °C 4: 80 percent / AlCl3 View Scheme

5-chloro-2-fluoroaniline (2106-05-0) → 2'-chloro-4',5'-difluoroacetophenone (121872-94-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: BF3*Et2O; t-BuONO / 1,2-dimethoxy-ethane / 1 h / -5 °C 2: 49 percent / 0.5 h / 170 °C 3: 80 percent / AlCl3 View Scheme

2,5-dichloronitrobenzene (89-61-2) + potassium-compound of 1-<4-hydroxy-phenyl>-ethanone → 2'-chloro-4',5'-difluoroacetophenone (121872-94-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: 52 percent / KF; 18-crown-6 / tetrahydrothiophene 1,1-dioxide / 32 h / 180 °C 2: H2 / 5 percent Pt/C / 1,2-dimethoxy-ethane / 24 h / 2585.74 Torr 3: BF3*Et2O; t-BuONO / 1,2-dimethoxy-ethane / 1 h / -5 °C 4: 49 percent / 0.5 h / 170 °C 5: 80 percent / AlCl3 View Scheme

2-Fluoro-5-chlorophenyldiazonium tetrafluoroborate → 2'-chloro-4',5'-difluoroacetophenone (121872-94-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 49 percent / 0.5 h / 170 °C 2: 80 percent / AlCl3 View Scheme

ortho-difluorobenzene (367-11-3) → 2'-chloro-4',5'-difluoroacetophenone (121872-94-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / FeCl3, Cl2 / 3 h / 50 °C 2: 75 percent / AlCl3 / 9 h / 60 °C View Scheme

carbonic acid dimethyl ester (616-38-6) + 2'-chloro-4',5'-difluoroacetophenone (121872-94-4) → methyl 3-(2-chloro-5-fluoro-4-methoxyphenyl)-3-oxopropanoate

Conditions	Yield
Stage #1: carbonic acid dimethyl ester With sodium hydride In tetrahydrofuran for 0.0833333h; Reflux; Stage #2: 2'-chloro-4',5'-difluoroacetophenone In tetrahydrofuran for 10h; Claisen Condensation; Reflux;	96%

2'-chloro-4',5'-difluoroacetophenone (121872-94-4) → 2-chloro-4,5-difluorobenzoic acid (110877-64-0)

Conditions	Yield
With sodium hypochlorite Oxidation;	90%
With hydrogenchloride; sodium hypochlorite In dichloromethane	85.1%
With hydrogenchloride; sodium hypochlorite In dichloromethane	85.1%
With sodium hypochlorite for 6h; Heating;	80%
With hydrogenchloride; sodium hydroxide; sodium hypobromide; bromine; sodium hydrogensulfite In 1,4-dioxane; dichloromethane; water

ethyl cyanoformate (623-49-4) + 2'-chloro-4',5'-difluoroacetophenone (121872-94-4) → 2-chloro-4,5-difluoro-β-oxobenzenepropanoic acid ethyl ester (121872-97-7)

Conditions	Yield
With hydrogenchloride; n-butyllithium; diisopropylamine In tetrahydrofuran; hexane	658 mg (61%)

2'-chloro-4',5'-difluoroacetophenone (121872-94-4) → 4-(2-chloro-5-fluoro-4-methoxyphenyl)-7-(diethylamino)-2H-chromen-2-one

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.08 h / Reflux 1.2: 10 h / Reflux 2.1: CoCl2(pyridine)2 / neat (no solvent) / 24 h / 110 °C / Inert atmosphere View Scheme

2'-chloro-4',5'-difluoroacetophenone (121872-94-4) → 7-(diethylamino)-4-(5-fluoro-4-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2H-chromen-2-one

Conditions

Yield

Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.08 h / Reflux 1.2: 10 h / Reflux 2.1: CoCl2(pyridine)2 / neat (no solvent) / 24 h / 110 °C / Inert atmosphere 3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / dichloromethane; tetrahydrofuran / 48 h / 105 °C / Sealed tube; Inert atmosphere View Scheme

2'-chloro-4',5'-difluoroacetophenone (121872-94-4) → 7-(diethylamino)-4-(5-fluoro-4-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-oxo-2H-chromene-3-carbaldehyde

Conditions

Yield

Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran / 0.08 h / Reflux 1.2: 10 h / Reflux 2.1: CoCl2(pyridine)2 / neat (no solvent) / 24 h / 110 °C / Inert atmosphere 3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / dichloromethane; tetrahydrofuran / 48 h / 105 °C / Sealed tube; Inert atmosphere 4.1: trichlorophosphate / 0.75 h / 0 °C / Inert atmosphere 4.2: 20.5 h / 0 - 20 °C / Inert atmosphere View Scheme

2'-chloro-4',5'-difluoroacetophenone (121872-94-4) → C8H3ClF2O2

Conditions	Yield
With selenium(IV) oxide In 1,4-dioxane; water for 4h; Reflux;

2'-chloro-4',5'-difluoroacetophenone (121872-94-4) → (2-chloro-4,5-difluorophenyl)(9H-pyrido[3,4-b]indol-1 yl)methanone

Conditions	Yield
Multi-step reaction with 2 steps 1: selenium(IV) oxide / 1,4-dioxane; water / 4 h / Reflux 2: palladium 10% on activated carbon / acetic acid / 3 h / Reflux View Scheme

2'-chloro-4',5'-difluoroacetophenone (121872-94-4) → 4,5-difluoro fascaplysin

Conditions	Yield
Multi-step reaction with 3 steps 1: selenium(IV) oxide / 1,4-dioxane; water / 4 h / Reflux 2: palladium 10% on activated carbon / acetic acid / 3 h / Reflux 3: 220 °C View Scheme

methylhydrazine (60-34-4) + 2'-chloro-4',5'-difluoroacetophenone (121872-94-4) → C9H9ClF2N2

Conditions	Yield
With magnesium sulfate In dichloromethane at 20℃;

2'-chloro-4',5'-difluoroacetophenone (121872-94-4) → (E)-3-((2-(1-(2-chloro-4,5-difluorophenyl)ethylidene)-1-methylhydrazineyl)sulfonyl)-N,N-dimethyl-1H-1,2,4-triazole-1-sulfonamide

Conditions	Yield
Multi-step reaction with 2 steps 1: magnesium sulfate / dichloromethane / 20 °C 2: pyridine / tetrahydrofuran / 0 - 20 °C View Scheme

Upstream product

• 367-11-3 ortho-difluorobenzene 
• 89-61-2 2,5-dichloronitrobenzene 
• 2106-05-0 5-chloro-2-fluoroaniline 
• 345-18-6 2-fluoro-5-chloronitrobenzene 
• 696-02-6 4-chloro-1,2-difluorobenzene 
• 75-36-5 acetyl chloride 

Downstream Products

• 121872-97-7 2-chloro-4,5-difluoro-β-oxobenzenepropanoic acid ethyl ester 
• 110877-64-0 2-chloro-4,5-difluorobenzoic acid 

Relevant academic research and scientific papers

Fluorinated benzoyl compounds

A 2-chloro-4,5-difluorobenzoyl compound of the formula: STR1 wherein R2 is a lower alkyl group, and R7 is a 2,4-difluorophenyl group or a 4-fluorophenyl group.