Tetrahydrofuran → HCID 72698334, compound

Participants

Reaction Steps

To a solution of methyl 2-bromo-4-methylbenzoate (10 g, 43.7 mmol) in THF (10 mL) was added dropwise EtMgBr (88 mL, 262 mmol) at 0° C. under nitrogen and then stirred at rt for 12 h. The reaction mixture was quenched with NH4Cl-saturated water and extracted with EA. The combined organic layer was washed with NaHCO3 solution and brine, dried over Na2SO4. The solution was concentrated and the residue was purified by column chromatography over silica gel eluted with PE-EA (10:1˜2:1) to provide 3-(2-bromo-4-methylphenyl)pentan-3-ol (8.09 g; yield 71.2%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.67 (d, 1 H), 7.52 (s, 1 H), 7.23 (d, 1 H), 2.35 (s, 3 H), 1.83 (m, 4 H), 0.77 (t, 6 H) ppm.

Provenance & Evidence