Lithium borohydride → HCID 69909280, compound

To a solution of methyl 2-bromo-4-chloro-5-methoxybenzoate (1.88 g, 6.7 mmol, Powers, J. J.; Favor, D. A.; Jeganathan, A.; Rankin, T.; Sharma, R.; Pandit, C.; Maiti, S, N. Tetrahedron Lett. 2009, 50(12), 1267-1269) in anhydrous THF (20 mL) was added lithium borohydride (0.644 g, 30 mmol). The resulting mixture was heated under reflux for about 72 h. After cooling to rt the mixture was concentrated in vacuo. The residue was partitioned between water (50 mL) and ethyl acetate (90 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (50 mL). The combined organic layers were washed with water (20 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, diethyl ether/hexanes 1:1) to give (2-bromo-4-chloro-5-methoxy-phenyl)methanol (1.57 g, 6.3 mmol, 93%) as a white solid: 1H-NMR (CDCl3, Bruker 400 MHz) δ 2.01 (1 H, t, J=6 Hz), 3.92 (3 H, s), 4.71 (2 H, d, J=6 Hz), 7.12 (1 H, s), 7.53 (1 H, s).

1. temperatureThe resulting mixture was heated
2. temperatureunder reflux for about 72 h
3. concentrationwas concentrated in vacuo
4. customThe residue was partitioned between water (50 mL) and ethyl acetate (90 mL)
5. customThe layers were separated
6. extractionthe aqueous layer was extracted with ethyl acetate (50 mL)
7. washThe combined organic layers were washed with water (20 mL)
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe residue was purified by column chromatography (SiO2, diethyl ether/hexanes 1:1)

ORD record

ord-e2473783a12a40129f95fb0c42fbcfbc

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150592B2