ChemicalBook CAS DataBase List 2,4-DIFLUORO-3-METHOXYBENZOYL CHLORIDE

2,4-DIFLUORO-3-METHOXYBENZOYL CHLORIDE synthesis

6synthesis methods

Product Name:2,4-DIFLUORO-3-METHOXYBENZOYL CHLORIDE
CAS Number:221221-11-0
Molecular formula:C8H5ClF2O2
Molecular Weight:206.57

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221221-11-0
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Yield:221221-11-0 100%

Reaction Conditions:

with thionyl chloride in dichloromethane;N,N-dimethyl-formamide at 20;Inert atmosphere;

Steps:

2,4-Difluoro-3-methoxybenzoyl chloride (16)

General procedure: Under inert atmosphere, a mixture of carboxylic acid 6-12 (Scheme 1) (1 equiv), thionyl chloride (1.5 equiv) and DMF (3-5 drops) in dichloromethane was stirred at rt until the complete consumption of the carboxylic acid (¹H NMR control). The pale yellow solution was concentrated in vacuo to give the crude acid chloride 13-19 (Scheme 1) as a yellow pale solid in quantitative yield and used without further purification in the condensation reaction with phenothiazine to provide compounds 20-26. ¹H NMR (CDCl₃, 400MHz) δ (ppm) 4.04 (s, 3H, OCH₃), 7.04 (td, J= 9.4, 2.0 Hz, 1H, ArH), 7.83 (sym m,1H, ArH). ¹⁹F NMR (CDCl₃,376 MHz) δ (ppm) -122.54 (dd, J = 18.4, 7.4 Hz, 1F, ArF),-114.80 (dddd, J = 18.4, 9.6, 5.4 Hz,1F, ArF).

References:

Abuhaie, Cristina-Maria;B?cu, Elena;Rigo, Beno?t;Gautret, Philippe;Belei, Dalila;Farce, Amaury;Dubois, Jo?lle;Ghinet, Alina [Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,# 1,p. 147 - 152] Location in patent:supporting information

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$23.50/1g