Lithium borohydride → 3-Bromo-4-iodobenzenemethanol

To a solution of methyl 3-bromo-4-iodobenzoate (110.0 mg, 0.322 mmol) in tetrahydrofuran (2 mL) was added 2 M lithium tetrahydroborate in tetrahydrofuran (0.161 mL) at room temperature. After stirring for 36 h, the reaction was quenched with sat. ammonium chloride solution, diluted with diethyl ether. The aqueous phase was extract with diethyl ether once. The combined organic solutions were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified with silica gel chromatography (5% to 20% ethyl acetate/hexane) to give a white solid (66 mg, 65%). 1H NMR (400 MHz, CDCl3): δ 7.82 (d, J=8.2 Hz, 1H), 7.63 (m, 1H), 6.98 (m, 1H), 4.63 (s, 2H). LCMS found for C7H5BrI (M+H−H2O)+: m/z=295, 297.

1. customthe reaction was quenched with sat. ammonium chloride solution
2. additiondiluted with diethyl ether
3. extractionThe aqueous phase was extract with diethyl ether once
4. dry with materialThe combined organic solutions were dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified with silica gel chromatography (5% to 20% ethyl acetate/hexane)

ORD record

ord-041cc6c6b55646d2bdb3be95c0bea49e

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07141596B2