Dimethyl Sulfoxide → rel-(1R,2R)-2-(4-Bromophenyl)cyclopropanecarboxaldehyde

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Reaction Steps

DMSO (0.8 mL, 3 equivalents) was added dropwise to a solution of oxalyl chloride (0.48 mL) in an hydrous dichloromethane (50 mL) under N2 at −78° C. A solution of (1R,2R)-[2-(4-bromophenyl)cyclopropyl]methanol (the product of Example 3A, 823 mg) in dichloromethane (20 mL) was then added dropwise at −78° C. Stirring at this temperature was continued for 30 minutes, then triethylamine (2 mL, 4 equivalents) was added and the dry ice bath was removed. After stirring for 1 hour, the mixture was treated with saturated aqueous NH4Cl. The mixture was extracted with diethyl ether. The combined organic extracts were dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by elution through a pad of silica gel with hexane to provide the title compound. 1H NMR (300 MHz, CDCl3): δ 1.48 (m, 1H), 1.65 (dt, J=9 Hz, J=6 Hz, 1H), 2.15 (m, 1H), 2.57 (m, 1H), 6.98 (d, J=9 Hz, 2H), 7.45 (d, J=9 Hz, 2H), 9.46 (d, J=4.5 Hz, 1H). MS (DCl—NH3) m/z 226 (M+H)+.

Provenance & Evidence