Dimethylformamide → 5-Bromo-2-fluorobenzoyl chloride

HRID 1662172Notes

Reaction equation

HRID 1662172 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].C(Cl)(=O)C([Cl:15])=O.CN(C=O)C>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([Cl:15])=[O:8]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 27363155-Bromo-2-fluorobenzoic acid

Product 1

HCID 219426655-Bromo-2-fluorobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-bromo-2-fluoro-benzoic acid (10.0 g, 45.7 mmol) in anhydrous dichloromethane (200 mL) was added oxalyl chloride (5.2 mL, 59.4 mmol) followed by addition of anhydrous DMF (0.2 mL). The reaction mixture was stirred at room temperature overnight, then concentrated to dryness in vacuo to give title compound in quantitative yield, which was used directly in the next step.

Workup

  1. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-d6c33355389444e08feb8e0537824c19
Source dataset
uspto-grants-2011_10
Patent number
US08030500B2

Reaction notes

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