Dimethylformamide → 3-Chloro-4-[(2,2,2-trifluoroethyl)oxy]benzoyl chloride

HRID 2192477Notes

Reaction equation

HRID 2192477 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[Cl:7][C:8]1[CH:9]=C([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][C:19]([F:22])([F:21])[F:20])C(O)=O.CN(C)C=O>ClCCl>[Cl:7][C:8]1[CH:9]=[C:1]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][C:19]([F:20])([F:21])[F:22])[C:2]([Cl:4])=[O:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 581498873-Chloro-4-(2,2,2-trifluoroethoxy)benzoic acid

Product 1

HCID 581498703-Chloro-4-[(2,2,2-trifluoroethyl)oxy]benzoyl chlorideYield 109.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.053 ml, 0.6 mmol) was added to a stirred solution of the 3-chloro-4-[(2,2,2-trifluoroethyl)oxy]benzoic acid (D20; 76 mg, 0.30 mmol) in dichloromethane (DCM) (2 ml) containing N,N-dimethylformamide (DMF) (0.02 ml) at 0° under nitrogen and the mixture was allowed to warm to room temperature with stirring overnight. The solvent was evaporated to give the title compound as a yellow solid (ca 90 mg) which was used crude in the next reaction (D48).

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-33fcfb215477410488bc9b0b1b5695aa
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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