Trifluoroacetic acid → 3-(4-Bromophenethoxy)propanoic acid

Participants

Reaction Steps

tert-Butyl 3-[2-(4-bromophenyl)ethoxy]propanoate (Example 10a), 1.0 g) was dissolved in dichloromethane (10 mL) and treated with trifluoroacetic acid (2.5 mL). The mixture was stirred at room temperature for 3 hours, then concentrated in vacuo and azeotroped with dichloromethane (2×10 mL). The residue was taken up in dichlormethane (10 mL) and extracted with 1M sodium hydroxide (20 mL). The basic layer was washed with dichloromethane (20 mL) then acidified with 2M hydrochloric acid. The acidic layer was extracted with dichloromethane (2×20 mL). The organic layers were combined, washed with brine, dried over anhydrous magnesium sulphate, filtered and concentrated to yield the sub-titled compound (0.81 g) as an oil.

Provenance & Evidence