Oxalyl chloride → 4-Bromo-2-chlorobenzoyl chloride

HRID 855316Notes

Reaction equation

HRID 855316 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[Br:7][C:8]1[CH:16]=[CH:15]C(C(O)=O)=[C:10]([Cl:17])[CH:9]=1>C(Cl)Cl.CN(C=O)C>[Br:7][C:8]1[CH:16]=[CH:15][C:1]([C:2]([Cl:4])=[O:3])=[C:10]([Cl:17])[CH:9]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 1088294-Bromo-2-chlorobenzoic acid

Product 1

HCID 155922074-Bromo-2-chlorobenzoyl chlorideYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Oxalylchloride (0.86 ml, 10.2 mmol) was added dropwise to a suspension of 4-bromo-2-chlorobenzoic acid (2.00 g, 8.5 mmol) in DCM (20 ml) at rt. After the addition of 5 drops of DMF, the reaction mixture was refluxed for 4 h, then cooled to rt and concentrated in vacuo to give 4-bromo-2-chloro-benzoyl chloride (2.15 g, 100%) which was used in the following step without further purification. 1H NMR (CDCl3, 300 MHz): δ 7.98 (d, J=8.5 Hz, 1H), 7.70 (d, J=2 Hz, 1H), 7.57 (dd, J=2 and 8 Hz 1H).

Workup

  1. temperaturethe reaction mixture was refluxed for 4 h
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-74344c3548274ed492d79885d5e8f0c9
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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