2,6-Lutidine → (S)-4-(2-bromo-1-(tert-butyldimethylsilyloxy)ethyl)benzonitrile

Participants

Reaction Steps

To a mixture of (S)-4-(2-bromo-1-hydroxyethyl)benzonitrile (6.9 g, 30.5 mmol) and 2,6-dimethylpyridine (7.82 mL, 67.1 mmol) in DCM (20 mL) was added t-butyl-dimethylsilyltrifluoromethanesulfonate (14.02 mL, 61.0 mmol). The reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate and washed with saturated NaCl. The organic layer was dried MgSO4, filtered and concentrated. The crude material was purified on a 80 gram silica column and eluting with an EtOAc/Hex gradient to afford 12 g of (S)-4-(2-bromo-1-(tert-butyldimethylsilyloxy)ethyl)benzonitrile. MS (M+1)=340/342. HPLC Peak RT=2.16 minutes. 1H NMR (400 MHz, CDCl3) δ ppm 7.65 (2H, d), 7.45 (2H, d), 4.88 (1H, dd), 3.42 (1H, q), 3.39 (1H, dd), 0.85 (9H, s), 0.12 (3H, s), −0.09 (3H, s).

Provenance & Evidence