Dimethylformamide → 2-Fluoro-3-(trifluoromethyl)benzoyl chloride

HRID 510232Notes

Reaction equation

HRID 510232 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[F:7][C:8]1[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:14]=[CH:13]C=1C(O)=O.CN(C=O)C>C(Cl)Cl>[F:7][C:8]1[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:14]=[CH:13][C:1]=1[C:2]([Cl:4])=[O:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 5180022-Fluoro-3-(trifluoromethyl)benzoic acid

Product 1

HCID 27375592-Fluoro-3-(trifluoromethyl)benzoyl chlorideYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.488 mL, 5.76 mmol) was added to a suspension of 2-fluoro-3-(trifluoromethyl)benzoic acid (1.00 g, 4.81 mmol) in DCM (10 mL) containing catalytic DMF. The reaction was stirred at room temperature for 90 minutes and solvents were removed in vacuo to afford the desired compound (1.08 g, 99%). The product was used without additional purification.

Workup

  1. customsolvents were removed in vacuo

Sources & evidence

ORD record
ord-050408838199402b9bf1d1e4faa20359
Source dataset
uspto-grants-2015_08
Patent number
US09096596B2

Reaction notes

Loading…