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

HRID 2206704Notes

Reaction equation

HRID 2206704 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-50c0644bf90848108afdfd7d25d56530
Source dataset
uspto-grants-2016_06
Patent number
US09371303B2

Reaction notes

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