Methyl 4-bromo-2-fluoro-6-hydroxybenzoate → 5-Bromo-3-fluoro-2-(hydroxymethyl)phenol

Temperature

0 °C

Methyl 4-bromo-2-fluoro-6-hydroxybenzoate (0.34 g, 1.4 mmol) was dissolved in dry THF (20 ml) under a blanket of nitrogen. The solution was cooled down to 0° C. and borane tetrahydrofuran complex (5.0 ml, 5.0 mmol) was slowly added. The mixture was stirred at 0° C. for 30 min and at ambient temperature for 15 min. Then it was cooled once more to 0° C. and carefully quenched with water, acidified with aqueous HCl (5%) and finally extracted several times with EtOAc. The combined organic phases were dried (Na2SO4), filtered and evaporated to dryness (0.33/g) to afford the title compound. No further purification was done on this intermediate. ESIMS: m/z 223 (M+H)+, 221 (M+H)+.

1. additionborane tetrahydrofuran complex (5.0 ml, 5.0 mmol) was slowly added
2. temperatureThen it was cooled once more to 0° C.
3. customcarefully quenched with water
4. dry with materialThe combined organic phases were dried (Na2SO4)
5. filtrationfiltered
6. customevaporated to dryness (0.33/g)

ORD record

ord-9f20f385b556469a9663c9717ac17db4

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08492372B2