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

Temperature

0 °C

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, 3 H) 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)

1. waitThe solution is left
2. dissolutionuntil dissolution of the aluminum complex
3. extractionThe desired product is extracted with ethyl acetate
4. washthe organic phase is washed with brine (200 mL)
5. dry with materialdried with MgSO4
6. concentrationconcentrated in vacuo

ORD record

ord-30b5f1853ae543459da8632d1ea767d0

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08093402B2