Iodine → (5-Bromo-2-chlorophenyl)methanol

5-bromo-2-chlorobenzoic acid (20 g, 84.92 mmol) in dry THF (50 mL) was added to a solution of sodium borohydride (8 g, 212.34 mmol) in dry THF (128 mL) in 15 min at r.t. To the resulting reaction mixture a solution of Iodine (26.85 g, 106.15 mmol) in dry THF (170 mL) was added in another 15 min. Stirring was continued till the Iodine color disappeared after which the reaction mixture was heated to reflux temperature for 18 h. After completion of the reaction as confirmed by TLC, volatiles were evaporated in vacuo. The residue obtained was dissolved in ethyl acetate (200 mL), washed with a saturated solution of NaHSO3 (200 mL) and brine (200 mL) successively. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford crude product which was purified by column chromatography (silica gel, 3:7 Ethyl acetate:Pet. Ether) to afford the title compound (18.3 g, 97%).

1. additionwas added in another 15 min
2. temperaturewas heated
3. temperatureto reflux temperature for 18 h
4. customAfter completion of the reaction
5. customwere evaporated in vacuo
6. customThe residue obtained
7. washwashed with a saturated solution of NaHSO3 (200 mL) and brine (200 mL) successively
8. dry with materialThe organic layer was dried over Na2SO4
9. concentrationconcentrated in vacuo
10. customto afford crude product which
11. customwas purified by column chromatography (silica gel, 3:7 Ethyl acetate:Pet. Ether)

ORD record

ord-ecc7be9abb60457595799bfa391b07e9

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018249B2