Dimethylformamide → 2-Bromo-5-chlorobenzoyl chloride

HRID 1695822Notes

Reaction equation

HRID 1695822 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4](O)=[O:5].CN(C=O)C.C(Cl)(=O)C([Cl:20])=O>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([Cl:20])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 890272-Bromo-5-chlorobenzoic acid

Product 1

HCID 205354252-Bromo-5-chlorobenzoyl chlorideYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-bromo-5-chlorobenzoic acid (8 g, 34.0 mmole) in dichloromethane (35 mL) was added DMF (1 mL) and oxalyl chloride (3.54 mL, 37.4 mmol) drop wise at 0° C. After complete addition, the reaction mixture was stirred at room temperature for 3 h. The volatiles were evaporated under reduced pressure to furnish 2-bromo-5-chloro-benzoyl chloride (8.5 g). The crude product was used without further purification.

Workup

  1. additionAfter complete addition
  2. customThe volatiles were evaporated under reduced pressure

Sources & evidence

ORD record
ord-0e118d9635484205b39f3cda2e22a1cd
Source dataset
uspto-grants-2012_04
Patent number
US08163704B2

Reaction notes

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