Dimethyl Sulfoxide → 2-(2,5-Difluorophenyl)cyclopropanecarbaldehyde

HRID 255225Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[CH:19]1[CH2:21][CH:20]1[CH2:22][OH:23].C(N(CC)CC)C>ClCCl>[F:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[CH:19]1[CH2:21][CH:20]1[CH:22]=[O:23]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of oxalyl chloride (1.2 mL, 13.5 mmol) in dichloromethane at −78° C. was added dimethyl sulfoxide (1.9 mL, 27 mmol) dropwise and it was stirred at −78° C. for 30 minutes. A solution of [2-(2,5-difluorophenyl)cyclopropyl]methanol (Intermediate 69) (830 mg, 4.5 mmol) in dichloromethane was added dropwise. The reaction mixture was stirred at −78° C. for 30 minutes. Triethylamine (6.3 mL, 45 mmol) was added and the reaction mixture was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure. Silica gel chromatography with hexanes/ethyl acetate (9:1) afforded the desired product, 546 mg (66%).

Workup

stirringThe reaction mixture was stirred at −78° C. for 30 minutes
stirringthe reaction mixture was stirred at room temperature for 2 hours
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-bb7ce860793f4ba1b2325caa4c3b1c2a
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875715B2

Reaction notes

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