Hydrochloric Acid → 2-(2-Bromophenyl)propan-2-ol

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of methyl 2-bromobenzoate (XCIV) (5 g, 0.0233 mol) in THF (30 mL) under argon at 0° C. was added dropwise MeMgBr (19.4 mL, 0.058 mol), maintaining the temperature in the range of −5 to 0° C. The reaction mixture was stirred at 0° C. for 1 hour and then at room temperature overnight. The mixture was cooled to 0° C. and 1M aqueous HCl (35 mL) was added, maintaining the temperature below 5° C., after which it was allowed to reach room temperature and was stirred for 30 minutes. To this mixture EtOAc (35 mL) was added and after stirring for 5 minutes a white precipitate was removed by filtration through a Celite pad. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic fractions were concentrated, washed with brine and dried over MgSO4. Crude XCV was purified by silica gel chromatography using DCM then DCM/MeOH 300/1 to give 2-(2-bromophenyl)propan-2-ol (XCV) as a light yellow oil (4.55 g; 21.2 mmol, 91% yield). 1H NMR (CDCl3) δ ppm 1.75 (s, 6H), 2.85 (brs, 1H), 7.09 (td, J=7 Hz, J=2 Hz, 1H), 7.29 (td, J=7 Hz, J=1 Hz, 1H), 7.58 (dd, J=7, J=1, 1H), 7.67 (dd J=7, J=2, 1H).

Provenance & Evidence