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

HRID 2192474Notes

Reaction equation

HRID 2192474 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][CH:19]1[CH2:21][CH2:20]1)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][CH:19]1[CH2:21][CH2:20]1)[C:2]([Cl:4])=[O:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 613797813-chloro-4-(cyclopropylmethoxy)Benzoic acid

Product 1

HCID 581498783-Chloro-4-[(cyclopropylmethyl)oxy]benzoyl chlorideYield 108.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.053 mL, 0.6 mmol) was added to a stirred solution of 3-chloro-4-[(cyclopropylmethyl)oxy]benzoic acid (WO 2005058848; 68 mg, 0.3 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 oil (ca 80 mg) which was used crude in the subsequent reaction (D46).

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-3096b31ae621475ba19eebfb2e9dc5ae
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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