Dimethylformamide → 4-Bromo-3-methylbenzoyl chloride

HRID 553690Notes

Reaction equation

HRID 553690 reaction equation
[Br: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>[Br: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 821314-Bromo-3-methylbenzoic acid

Product 1

HCID 70215344-Bromo-3-methylbenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-bromo-3-methylbenzoic acid (8.6 g, 40.0 mmol) in CH2Cl2 was added DMF (0.4 mL), followed by oxalyl chloride (3.7 mL, 42 mmol) slowly over 10 minutes by syringe. The reaction was stirred for 1 hour at room temperature, and then concentrated to give the title compound.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-db03c296492f4a5e91b55b50031f5db2
Source dataset
uspto-grants-2011_11
Patent number
US08048902B2

Reaction notes

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