ChemicalBook CAS DataBase List 2-Chlorobenzoyl chloride

2-Chlorobenzoyl chloride synthesis

11synthesis methods

Product Name:2-Chlorobenzoyl chloride
CAS Number:609-65-4
Molecular formula:C7H4Cl2O
Molecular Weight:175.01

A process for preparing 2-chlorobenzoyl chloride which comprises reacting 2-chlorobenzaldehyde with chlorine in the presence of phosphorus pentachloride at a temperature of from 50° to 200° C. and wherein the 2-chlorobenzaldehyde: phosphorus pentachloride ratio is from 1:0.05 to 1:0.2. Phosphorus pentachloride (41.5 g, 0.2 mole) was added to 2-chlorobenzaldehyde (289.7 g, 2.0 mole, 97%). After the ensuing exotherm had subsided, the resulting red solution was heated to 160° C. A stream of chlorine was introduced through a sparge tube into the solution for six hours. (Gas chromatography indicated 96.5% conversion.) The solution was then cooled and distilled under reduced pressure, giving 325.4 grams of 2-chlorobenzoyl chloride, which boiled at 135° to 140° C. at 16 millimeters of mercury. The yield of 2-Chlorobenzoyl chloride was 93% (98.5% pure).

118-91-2 Synthesis

118-91-2
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609-65-4
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$19.00/25mL

Yield:609-65-4 100%

Reaction Conditions:

with thionyl chloride in toluene at 75;

Steps:

1
Into a 500 mL round bottom flask was placed a solution of 2-chlorobenzoic acid (20 g, 127.80 mmol) in toluene (150 mL). To the mixture was added SOCl₂ (16 g, 134.45 mmol). The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at 75 ⁰C in a bath of oil. The mixture was concentrated by evaporation under vacuum using a rotary evaporator. This resulted in 22.3 g (100%) of 2-chlorobenzoyl chloride as yellow oil.

References:

MEMORY PHARMACEUTICALS CORPORATION WO2007/98418, 2007, A1 Location in patent:Page/Page column 113-114

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104-86-9 Synthesis