Dimethylformamide → 4-Bromo-2-fluorobenzoyl chloride

HRID 520311Notes

Reaction equation

HRID 520311 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([F:11])[CH:3]=1.C(Cl)(=O)C([Cl:15])=O.CN(C=O)C>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:15])=[O:7])=[C:4]([F:11])[CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 3026814-Bromo-2-fluorobenzoic acid

Product 1

HCID 27340264-Bromo-2-fluorobenzoyl chlorideYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-2-fluorobenzoic acid 144a (250 g, 1.14 mol) in dry DCM (2000 mL) was added oxalyl chloride (446 g, 3.51 mol) and DMF (10 mL) at RT, and the reaction mixture was stirred at RT for 1 h. See FIG. 3. The mixture was concentrated under reduced pressure to give 4-bromo-2-fluorobenzoyl chloride 144b (271 g, 100%) as a yellow solid, which was used for the next step without further purification.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-54e8f043908945eba44edd67a3401a95
Source dataset
uspto-grants-2016_05
Patent number
US09326985B2

Reaction notes

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