Methanol → Tert-butyl 3-bromo-5-(hydroxymethyl)benzoate

Temperature

0 °C

To a solution of tert-butyl methyl 5-bromoisophthalate (3.63 g, 11.5 mmol) in tetrahydrofuran (90 mL) at 0° C. was added portionwise sodium borohydride (1.53 g, 40.3 mmol). The mixture was stirred at 0° C. After 30 min, methanol (4.2 mL, 92.0 mmol) was added and the mixture was heated to 40° C. After 6 h, the mixture was cooled to ambient temperature and the mixture was quenched with methanol and concentrated. Ethyl acetate was added and the mixture was washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→50% hexanes/ethyl acetate) gave the title compound (2.7 g).

1. temperaturethe mixture was heated to 40° C
2. waitAfter 6 h
3. temperaturethe mixture was cooled to ambient temperature
4. customthe mixture was quenched with methanol
5. concentrationconcentrated
6. additionEthyl acetate was added
7. washthe mixture was washed with brine
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customPurification by silica gel chromatography (100% hexanes→50% hexanes/ethyl acetate)

ORD record

ord-58805491a88f4125a5c9b26f9c6f4aec

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08461185B2