Hydrochloric Acid → (4-Bromo-3-methylphenyl)methanol

Participants

Reaction Conditions

Reaction Steps

Methyl 4-bromo-3-methylbenzoate (17.0 g, 74.2 mmol) is dissolved in anhydrous THF (100 mL). The solution is cooled to 0° C. and a 2 M solution of lithium aluminum hydride in THF (40 mL) is added to the mixture. The solution is left stirring 30 min. at this temperature. A cold HCl solution is then added drop wise to the reaction mixture until dissolution of the aluminum complex. The desired product is extracted with ethyl acetate, the organic phase is washed with brine (200 mL), dried with MgSO4 and concentrated in vacuo. to provide the expected product (4-Bromo-3-methylphenyl)methanol (14.4 g, 97%) as a clear yellow oil, pure by proton NMR, and is used as such in the next step. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 2.40 (s, 3H) 4.61 (s, 2H) 6.89-7.10 (m, J=8.20, 1.56, 0.59 Hz, 1H) 7.23 (d, J=2.34 Hz, 1H) 7.50 (d, J=8.20 Hz, 1H)

Provenance & Evidence