t-Butyl bromide → Methyl 2-(1-benzothiophen-3-yl)-2-(tert-butoxy)acetate

Participants

Reaction Steps

A mixture of methyl 2-(1-benzothiophen-3-yl)-2-hydroxyacetate (4a) (300 mg, 1.35 mmol), silver (I) oxide (938 mg, 4.05 mmol) and tertbutylbromide (910 μL, 8.1 mmol) in a mixture of cyclohexane (5 mL) and dichloromethane (1 mL) was vigorously stirred for 20 hours under a nitrogen atmosphere. The reaction mixture was then filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to afford the desired ether oxide (4b) as a white solid (70 mg, 0.25 mmol, 10%).

Provenance & Evidence