Dimethylformamide → 3-Chloro-4-[(difluoromethyl)oxy]benzoyl chloride

HRID 2192475Notes

Reaction equation

HRID 2192475 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH:12]([F:14])[F:13])[C:5](O)=[O:6].C(Cl)(=O)C([Cl:18])=O.CN(C)C=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH:12]([F:14])[F:13])[C:5]([Cl:18])=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 581499323-Chloro-4-(difluoromethoxy)benzoic acid

Product 1

HCID 581499223-Chloro-4-[(difluoromethyl)oxy]benzoyl chlorideYield 125.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloro-4-[(difluoromethyl)oxy]benzoic acid (D17; 0.28 g, 1.258 mmol) was stirred at room temperature with oxalyl chloride (0.220 mL, 2.52 mmol) and N,N-dimethylformamide (DMF) (0.05 ml) in dry dichloromethane (DCM) (5 ml) under nitrogen for 16 h. The solvent was evaporated in vacuo to give a yellow semi-solid (380 mg) which was used crude in the subsequent reaction D47.

Workup

  1. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-65426e63b3224c6a8ff4f11149b4bb70
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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