Benzyl Bromide → HCID 59434260, compound

Participants

Reaction Conditions

Reaction Steps

To a 250-mL 3-necked round bottomed flask equipped with a mechanical stirrer and a thermometer was charged 75 (35 g, 0.1 moles) and THF (60 mL) under an atmosphere of argon. NaH (6 g, 60%, mineral oil suspension, 0.15 moles) was added to the solution. The mixture was heated at 60° C. for 1 hour and then cooled to room temperature. Benzyl bromide (23.8 mL, 0.2 moles) and tetrabutylammonium bromide (10 g, 0.03 moles) were added to the suspension. The reaction mixture was heated at 70° C. for 6 hours and then the reaction mixture was cooled to room temperature. 1,9-diazabicyclo[5.4.0]undecen-7-ene (45 mL, 0.2 moles) was added and heated at 50° C. for 45 min. The reaction mixture was cooled to room temperature, quenched with 1N HCl to pH ˜1 and extracted with a mixture of EtOAc-hexane (250 mL). The organic layer was washed with water (500 mL), brine (100 mL) and concentrated in vacuo to afford the title compound (42 g) as a brown oil.

Provenance & Evidence