Dimethyl Sulfoxide → trans-2-(4-Bromophenyl)cyclopropane-1-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (17.50 mL, 2 M in DCM, 35.0 mmol) in DCM (150 mL) under nitrogen atmosphere and cooled to −78° C. was added dropwise DMSO (4.97 mL, 70.0 mmol), followed with the dropwise addition of a solution of the product from Example 34D, ((1S,2S)-2-(4-bromophenyl)cyclopropyl)methanol (5.3 g, 23.34 mmol) in DCM (100 mL). The mixture was stirred 30 minutes at −78° C. Then the mixture was treated with triethylamine (13.01 mL, 93 mmol), and then the reaction temperature was raised to ambient temperature. The mixture was partitioned between DCM (400 mL) and H2O (400 mL). The organic layer was separated, washed with water, dried and concentrated under reduced pressure to provide the title product. 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