Benzyl Bromide → (E)-1-(3(benzyloxy)prop-1enyl)2-chlorobenzene

Participants

Reaction Steps

To a solution of (E)-3-(2-chlorophenyl) prop-2-en-1-ol(Preparation example 1, 5.3 g, 31.6 mmole) in THF was added NaH (60% in mineral oil, 0.91 g, 37.7 mmole) and Benzyl bromide (4.12 mL, 34.8 mmole), sequently at 0° C. The reaction mixture was stirred at room temperature for 18 hr. The TLC showed complete consumption of SM. The reaction mixture was quenched with H2O at 0° C. then extracted with EtOAc. The aqueous layer was extracted with EtOAc and separated. The combined organic layer was washed with H2O, then dried over MgSO4 and evaporated under reduced pressure. The crude compound was purified by silica ge column to produce the title compound (4.94 g, 70˜90%).

Provenance & Evidence