Carbon tetrabromide → HCID 5363780, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 460 mg (2.0 mmol) of (E)-3-methyl-4-(tetrahydro-2H-pyran-2-yloxy)but-2-enyl acetate in 20 ml of CH2Cl2 was added a solution of 1.33 g (4 mmol) of CBr4 in 10 ml of CH2Cl2. The solution was cooled to 0° C. and a solution of 1.05 g (4 mmol) of triphenylphosphine was added dropwise. The solution was allowed to warm up to room temperature for 6 hours and stirred at the same temperature for further 1 hour. The precipitate was filtered and the filtrate was evaporated. The residue was purified by chromatography on silica gel using Heptane/EtOAc (8/2) as eluent. 314 mg (1.52 mmol, 76%) of (E)-4-bromo-3-methylbut-2-enyl acetate were isolated as colourless oil.

Provenance & Evidence