Dimethylformamide → 4-Chloro-3-methylbenzoyl chloride

HRID 132903

Reaction equation

HRID 132903 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[CH3:11].CN(C=O)C.C(Cl)(=O)C([Cl:20])=O>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:20])=[O:7])=[CH:4][C:3]=1[CH3:11]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 2829894-Chloro-3-methylbenzoic acid

Product 1

HCID 130583754-Chloro-3-methylbenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 52.55 g (0.31 mol) of 4-chloro-3-methyl-benzoic acid in CH2Cl2 (1.2 L) with DMF (1 mL) at 0° C. under N2 with an outlet sparging through 2.5 N sodium hydroxide was added 29.56 mL (0.339 mol) of oxalyl chloride. The mixture was allowed to warm to room temperature over a 3 h period. The reaction mixture was concentrated and taken forward crude.

Workup

  1. customsparging through 2.5 N sodium hydroxide
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-04efb45b1d8c4d0fbf9c78969fce8285
Source dataset
uspto-grants-2008_06
Patent number
US07388011B2

Linked notes

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