Dimethylformamide → 4-Bromo-2-methoxybenzoyl chloride

HRID 2391096Notes

Reaction equation

HRID 2391096 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1.CN(C=O)C.S(Cl)([Cl:20])=O>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:20])=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 134507554-Bromo-2-methoxybenzoic acid

Product 1

HCID 223467824-Bromo-2-methoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
55 °C

Procedure

To a suspension of 4-bromo-2-methoxybenzoic acid (2.5 g, 11.04 mmol) in CHCl3 (20 mL) was added DMF (catalytic) and thionyl chloride (1.6 mL, 22.08 mmol). The reaction was stirred at 55° C. for 1 hour and then concentrated to dryness to give the title compound.

Workup

  1. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8b47489dc57246cf96b26ed6e7971051
Source dataset
uspto-grants-2012_09
Patent number
US08273780B2

Reaction notes

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