Benzyl Bromide → HCID 19918600, compound

Participants

Reaction Steps

To a stirred solution of the above (18) (6.1 g) in dry THF (100 mL) at -78° C. was added a solution of lithium bis-trimethylsilylamide (50 ml, 1N in THF). The solution was stirred for 20 min then benzylbromide (30 mL) was added in one portion. The reaction was stirred for 6 h at -78° C. then allowed to slowly warm to room temperature. After evaporation of the solvent, the remaining mixture was taken up in hexane, washed with saturated NaCl, dried over MgSO4 and evaporated. The product (19) was obtained by flash chromatography on silica gel eluted with 2.5% ethyl acetate in hexane. (4.15 g, 39%): GC RT 7.29 min. (HP 530 mμ×20 m methylsilicone column, He carrier flow rate 20 mL/min., 100° C., 1 min. , 100°-180° C. 10° C./min.; TLC Rf 0.31 (5% ethyl acetate, n-hexane); 1H NMR (CDCl3) δ1.73(3H, br s), 2.2-3.3(7H, m), 5.35(1H, br s), 7.28(5H, m).

Provenance & Evidence