Methanol → (3-Bromo-2-fluoro-4-methoxyphenyl)methanol

In a 100 mL round bottomed flask equipped with a stir bar was placed 3-bromo-2-fluoro-4-methoxy-benzaldehyde (I-30, 1.67 g, 7.17 mmol), methanol (12 mL), dichloromethane (12 mL) and sodium borohydride. The reaction mixture was allowed to stir at room temperature for 17 hours, quenched with water (10 mL) and 1M HCl (5 mL) and extracted with dichloromethane (2×30 mL). The organic portions were combined, washed with brine (30 mL), dried (MgSO4) and concentrated. The crude material was triturated with hexanes (15 mL) to produce 955 mg (57%) of (3-bromo-2-fluoro-4-methoxy-phenyl)-methanol (I-31) as a white solid.

1. customIn a 100 mL round bottomed flask equipped with a stir bar
2. customquenched with water (10 mL) and 1M HCl (5 mL)
3. extractionextracted with dichloromethane (2×30 mL)
4. washwashed with brine (30 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated
7. customThe crude material was triturated with hexanes (15 mL)

ORD record

ord-e15cd109d0704d4fb605aab561099e7f

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08791267B2