Dimethylformamide → 3-Bromo-4-chlorobenzoyl chloride

HRID 661609Notes

Reaction equation

HRID 661609 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5](O)=[O:6].CN(C=O)C.C(Cl)(=O)C([Cl:20])=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([Cl:20])=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 27355443-Bromo-4-chlorobenzoic acid

Product 1

HCID 202297303-Bromo-4-chlorobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-bromo-4-chloro-benzoic acid (9.4 g, 40 mmol) in dry DCM (100 mL), was added DMF (0.5 mL) followed by addition of oxalyl chloride (22.5 mL, 55 mmol, 2M in DCM) slowly. The mixture was stirred for 1 hr, then concentrated to yield 3-bromo-4-chloro-benzoyl chloride as an off-white solid.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-8e24efe67aea44ecaa63baa40ff628ba
Source dataset
uspto-grants-2011_12
Patent number
US08084614B2

Reaction notes

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