Dimethylformamide → 5-Bromo-2-chloro-3-methoxybenzoyl chloride

HRID 576331Notes

Reaction equation

HRID 576331 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].CN(C=O)C.C(Cl)(C([Cl:23])=O)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([Cl:23])=[O:8]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 710769615-Bromo-2-chloro-3-methoxybenzoic acid

Product 1

HCID 867140435-Bromo-2-chloro-3-methoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 56 (3.82 g, 14.3 mmol) in CH2Cl2 (63 mL) was added dropwise DMF (0.20 mL) and (COCl)2 (1.63 mL, 18.7 mmol) at 0° C. under an atmosphere of nitrogen. After being stirred for 20 hours at room temperature, the mixture was concentrated in vacuo to provide the crude acid chloride 59, which was used for the next reaction without further purification.

Workup

  1. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-280873cd8a2c49c5b4742bcdb518c8ce
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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