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

Temperature

-78 °C

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 dro wise DMSO (4.97 mL, 70.0 mmol), followed with the dropwise addition of a solution of the product from Example 8D, ((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 (DCI—NH3) m/z 226 (M+H)+.

1. temperaturethe reaction temperature was raised to ambient temperature
2. customThe mixture was partitioned between DCM (400 mL) and H2O (400 mL)
3. customThe organic layer was separated
4. washwashed with water
5. customdried
6. concentrationconcentrated under reduced pressure

ORD record

ord-be757c941f954a50a87c4fa2da5f2dee

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09186353B2