1-Bromo-3-fluorobenzene → HCID 57893757, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve 1-methyl-piperidin-4-ol (10.06 g, 87.34 mmol) in DMF (30 mL) and add to a stirred suspension of sodium hydride (5.24 g, 131.01 mmol) in DMF (155 mL). After the addition is complete, heat at 50° C. After 45 min., add a solution of 1-bromo-3-fluoro-benzene (12.2 mL, 109.18 mmol) in DMF (15 mL) and stir and heat at 65° C. After 18 hr., cool to ambient temperature, quench with water (5 mL), remove the DMF under reduced pressure, wash with water (50 mL) and extract with ethyl acetate/hexanes (2/1 mixture, 2×35 mL). Combine the organic layers, dry over magnesium sulfate, filter under reduced vacuum and concentrate to dryness. Purify by flash chromatography using dichloromethane/ammonia (2.0M in methanol) 20/1 as the eluent to give of the title compound (15.4 g, 65%). Mass spectrum (ion spray): m/z=270.0 (M+1); 1H NMR (CDCl3): 7.12 (t, J=8.3 Hz, 1H), 7.07-7.04 (m, 2H), 6.83 (bd, J=8.3 Hz, 1H), 4.35-4.26 (bm, 1H), 2.73-2.64 (bm, 2H), 2.37-2.28 (bm, 5H), 2.05-1.96 (bm, 2H), 1.89-1.79 (bm, 2H).

Provenance & Evidence