Dimethylformamide → 3-Bromo-4-chlorobenzoyl chloride

HRID 1848567Notes

Reaction equation

HRID 1848567 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-81df8ea0845140d1bc75193118dc866d
Source dataset
uspto-grants-2015_02
Patent number
US08952161B2

Reaction notes

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