Oxalyl chloride → 1-(4-Chlorophenyl)cyclopropane-1-carbonyl chloride

HRID 1174662Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:17])=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([Cl:17])=[O:13])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A catalytic amount of N,N-dimethylformamide (DMF)(10 μL) was added to a mixture of 1-(4-chlorophenyl)cyclopropanecarboxylic acid (1.0 g, 5.1 mmol) and oxalyl chloride (2.2 mL, 25 mmol) in methylene chloride (5 mL) at 0° C. The resulting mixture was stirred at room temperature (about 25° C.) for 2 h. The volatiles were removed under reduced pressure, and the resulting residue was co-evaporated with toluene (2×) to provide the crude product, 1-(4-chlorophenyl)cyclopropanecarbonyl chloride, which was used in next step without further purification.

Workup

customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record: ord-399f0dc83f4745878669cf10dce0a76b
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07838544B2

Reaction notes

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