Thiophene → 3-Chloro-1-(2-thienyl)-1-propanone

Temperature

-5 °C

Chloropropionyl chloride (12 mL, 130 mmol) in dry dichloromethane (50 mL) was added dropwise at −5° C. to a stirred suspension of aluminium chloride (18.8 g, 141 mmol) in dry dichloromethane (100 mL). The resulting suspension was allowed to stir at −5° C. for 10 mins before a solution of thiophene (10 g, 118 mmol) in dry dichloromethane (50 mL) was added dropwise. The resulting orange solution was stirred at −5° C. for 1 hr before being carefully dropped onto crushed ice (200 g). The organic phase was separated and dried (MgSO4), the solvent was then passed through a pad of celite/charcoal to remove any colour. Removal of the solvent in vacuo resulted in the title compound as a colourless oil (20 g, 100%); δH (300 MHz, CDCl3) 7.75 (1H, d, Ar), 7.68 (1H, d, Ar), 7.15 (1H, m, Ar), 3.90 (2H, t, J=7 Hz, CH2), 3.38 (2H, t, J=7 Hz, CH2).

1. additionwas added dropwise
2. additionbefore being carefully dropped
3. customThe organic phase was separated
4. dry with materialdried (MgSO4)
5. customto remove any colour
6. customRemoval of the solvent in vacuo

ORD record

ord-94055bb67fc24defb7cfaf63727c8e80

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07037932B2