2-Bromopropane → HCID 21243558, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 3-hydroxy-5-phenyl-2-thiophenecarboxylate (20.0 g, 85 mmoles) is dissolved in dimethylsulfoxide (80 mL) under argon and cooled in an ice bath. Potassium t-butoxide (10.1 g, 90 mmoles) is added, followed after 25 minutes by 2-bromopropane (22.1 g, 180 mmoles), and the ice bath is removed. After 24 hours the mixture is heated to 80° C. for 1 hour, then poured into ice water (500 mL), stirred, and acidified with concentrated HCl. The mixture is extracted with dichloromethane (3×200 mL) and the combined extracts are washed with brine, dried over MgSO4 and stripped of solvent under reduced pressure to leave the product as a syrupy residue (22.1 g) sufficiently pure for further use.

Provenance & Evidence