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

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 (1S,2S)-[2-(4-bromophenyl)cyclopropyl]methanol (the product from Example 1B, 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 twice. 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, CDC3): 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 twice
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レコード

ord-13adbc038cf74667a10d1e1c39b353b2

出典データセット

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08829041B2