Oxalyl chloride → 4-Bromo-2-methylbenzoyl chloride

HRID 1671353Notes

Reaction equation

HRID 1671353 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[Br:7][C:8]1[CH:16]=[CH:15][C:11](C(O)=O)=[C:10](C)[CH:9]=1>CN(C=O)C.C(Cl)Cl>[Br:7][C:8]1[CH:16]=[CH:15][C:1]([C:2]([Cl:4])=[O:3])=[C:10]([CH3:11])[CH:9]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 128464834-Bromo-2-methylbenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

DMF (1 drop) and oxalyl chloride (0.44 ml, 5.0 mmol) are added to a stirred suspension of 4-bromo-2-methylbenzoic acid (0.90 g, 4.19 mmol) in dry DCM (10 ml). The reaction is stirred for 3 h at RT when a clear solution is obtained. The solvent is removed in vacuo to give the title product as an oil which crystallised. This is used in the next step without purification.

Workup

  1. customis obtained
  2. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-3f49e8079cbc4770ae1c50ffdb9ed288
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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