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

DMSO (0.8 mL, 3 equivalents) was added dropwise to a solution of oxalyl chloride (0.48 mL) in anhydrous 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)+.

1. customthe dry ice bath was removed
2. stirringAfter stirring for 1 hour
3. additionthe mixture was treated with saturated aqueous NH4Cl
4. extractionThe mixture was extracted with diethyl ether
5. dry with materialThe combined organic extracts were dried (MgSO4)
6. filtrationfiltered
7. concentrationThe filtrate was concentrated under reduced pressure
8. customThe residue was purified by elution through a pad of silica gel with hexane

ORD record

ord-6bb1b07ccfab48ddbc2084decec0f862

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08829041B2