Dimethyl Sulfoxide → 3-(4-Fluorophenyl)propanal

Temperature

-78 °C

A solution of oxalyl chloride (1.32 mL, 15.1 mmol) in dichloromethane (40 mL) was stirred at −78° C. and treated dropwise with dimethyl sulfoxide (2.21 mL, 31.1 mL) over 5 minutes. The resulting solution was stirred for 35 minutes at −78° C. A solution of 3-(4-fluorophenyl)-propan-1-ol (1.50 g, 9.73 mmol) in dichloromethane (12 mL) was added over 5 minutes, and stirring continued at the same temperature for 50 minutes. Triethylamine (4.41 mL, 31.6 mmol) was added, and the cooling bath was replaced by an ice-water bath. The resulting slurry was stirred for one hour, then was diluted with dichloromethane. The resulting mixture was washed with half-saturated aqueous ammonium chloride, then with saturated sodium chloride, dried over sodium sulfate, and concentrated under vacuum. The resulting orange oil was distilled in a short-path apparatus at 50° C. and 0.2 Torr pressure to provide a colorless liquid (764 mg, 50%). 1H NMR (300 MHz, CDCl3) δ9.83 (t, J=1 Hz, 1H), 7.17 (m, 2H), 6.99 (t, J=9 Hz, 2H), 2.95 (t, J=7 Hz, 2H), 2.79 (tt, J=7, 1 Hz, 2H).

1. stirringstirring
2. waitcontinued at the same temperature for 50 minutes
3. customthe cooling bath was replaced by an ice-water bath
4. stirringThe resulting slurry was stirred for one hour
5. washThe resulting mixture was washed with half-saturated aqueous ammonium chloride
6. dry with materialwith saturated sodium chloride, dried over sodium sulfate
7. concentrationconcentrated under vacuum
8. distillationThe resulting orange oil was distilled in a short-path apparatus at 50° C.

ORD record

ord-83b1eff5aded4809bda63eb9b928a8e2

Source dataset

uspto-grants-2005_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06919356B2