Triphenylphosphine → 1-Bromo-4-[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]methoxy-3-fluorobenzene

Participants

Reaction Steps

To a stirred solution of 4-bromo-2-fluorophenol (217 ul, 2.002 mmol), N-tert-butoxycarbonyl prolinol (403 mg, 2.002 mmol), and Ph3P (630 mg, 2.403 mmol) in THF (7 mL) was added DIAD (477 ul, 2.423 mmol) at room temp. The resulting mixture was stirred for 6 hr at room temp and then overnight at 70° C. The mixture was concentrated in vacuo and the residue was chromatographed on silica-gel with n-hexane-EtOAc (5:1, v/v) as eluent to give 549.4 mg (73%) 1-bromo-4-[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]methoxy-3-fluorobenzene as an oil. 1H-NMR (400 MHz, CDCl3) δ1.46 (s, 9H), 1.85 (br m, 1H), 1.90-2.10 (br s, 3H), 3.30-3.47 (m, 2H), 3.85, 4.04 (br s each, 1H), 4.11-4.20 (m, 2H), 6.82-6.98 (m, 1H), 7.13-7.26 (m, 2H); MS (FAB) m/z 374 (M++1).

Provenance & Evidence