Sodium borohydride → HCID 58762592, compound

Temperature

0 °C

Bromine (15 mL, 0.3 mol) was added slowly to a solution of 2-fluoro-5-methoxy-benzaldehyde (23.1 g, 0.15 mol) in chloroform (500 mL) and the mixture was stirred at room temperature for 5 days. The mixture was poured into water (200 ml) and extracted with chloroform (2×200 mL). The organics were washed with water, brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash column chromatography (2-16% EtOAc in hexanes to give 4-bromo-2-fluoro-methoxy-benzaldehyde (20.7 g, 60%). To a solution of 4-bromo-2-fluoro-5-methoxy-benzaldeyde (4.0 g, 17.3 mmol) in MeOH at 0° C. was added NaBH4 (0.65 g, 17.3 mmol). After the reaction mixture was stirred at 0° C. for 2 hours, it was allowed to warm to room temperature. The organic layer was taked up in ethyl ether washed with water and dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (25-45% EtOAc in hexanes) to give the product. (3.9 g, 99%). 1H NMR (300 MHz, CDCl3): δ 3.90 (s, 3H), 4.74 (d, J=6.02 Hz, 2H), 6.82 (q, J=6.1 Hz, 1H), 7.29 (d, J=10.58 Hz, 1H).

1. temperatureto warm to room temperature
2. washwashed with water
3. dry with materialdried over MgSO4
4. filtrationfiltered
5. concentrationconcentrated
6. customThe residue was purified by flash chromatography (25-45% EtOAc in hexanes)
7. customto give the product

ORD record

ord-613fe8ada6b94c90926fa289f918630f

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622605B2