Water → (5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanol

To a suitable reaction flask was charged (5-bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone (103.06 mmoles, 35.00 g) and acetonitrile (6.68 moles, 350.00 mL, 274.15 g) to afford a clear solution. The solution was cooled to 0 degrees Celsius and sodium borohydride (128.82 mmoles, 4.87 g) was added portionwise. The reaction was stirred for approximately 30 minutes at 0 degrees Celsius, and then at room temperature until completion (as determined by HPLC analysis). To the reaction mixture was then added water (40 mL), followed by brine (50 mL). The layers were shaken together, allowed to settle and then were separated. The organic phase was concentrated to an oil. Methyl tert-butyl ether (200 mL) was added followed by a slow addition of 1N hydrochloric acid. Vigorous gas evolution was observed. The layers were shaken together, allowed to settle and then were separated. The organic phase was washed with brine (50 mL), dried over magnesium sulfate, filtered and concentrated to afford the crude product as a pale yellow solid (35.38 g, 100% yield).

1. customto afford a clear solution
2. temperatureThe solution was cooled to 0 degrees Celsius
3. customat room temperature
4. stirringThe layers were shaken together
5. customwere separated
6. concentrationThe organic phase was concentrated to an oil
7. additionMethyl tert-butyl ether (200 mL) was added
8. additionfollowed by a slow addition of 1N hydrochloric acid
9. stirringThe layers were shaken together
10. customwere separated
11. washThe organic phase was washed with brine (50 mL)
12. dry with materialdried over magnesium sulfate
13. filtrationfiltered
14. concentrationconcentrated

ORD record

ord-dd6f581a3e6946f1a3a3f97441f2a2a3

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09308204B2