Methanol → (4-Chloro-3-iodophenyl)methanol

Borane-THF complex (10 ml) was added dropwise over 20 minutes to a solution of 4-chloro-3-iodobenzoic acid (1.4 g) in THF (25 ml). The reaction mixture was stirred for 2 hours and then cooled (ice bath) and methanol (20 ml) was added cautiously. The solvent was removed and the residue was dissolved in methanol (10 ml) and stirred with aq. 2M sodium hydroxide (10 ml) for 2 hours. Ethyl acetate (50 ml) was added and the mixture was washed with saturated aq. sodium bicarbonate solution (50 ml). The aqueous extracts were washed with ethyl acetate (2×50 ml) and the combined ethyl acetate extracts were washed with water (50 ml) and brine (50 ml) and died. Removal of the solvent gave 4-chloro-3-iodobenzyl alcohol (1.15 g). NMR (CD3SOCD3): d 4.45 (d, 2H), 5.3 (t, 1H), 7.3 (m, 1H), 7.5 (m, 1H), 7.8 (s, 1H).

1. additionwas added cautiously
2. customThe solvent was removed
3. dissolutionthe residue was dissolved in methanol (10 ml)
4. stirringstirred with aq. 2M sodium hydroxide (10 ml) for 2 hours
5. additionEthyl acetate (50 ml) was added
6. washthe mixture was washed with saturated aq. sodium bicarbonate solution (50 ml)
7. washThe aqueous extracts were washed with ethyl acetate (2×50 ml)
8. washthe combined ethyl acetate extracts were washed with water (50 ml) and brine (50 ml)
9. customRemoval of the solvent

ORD record

ord-b10c841420ea4d5b98a95b4da96cb1d8

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06984657B1