Methanol → 2-Fluoro-3-iodo-4-methylbenzaldehyde

To a solution of 2-fluoro-3-iodo-4-methylbenzoic acid (2.00 g, 7.1 mmol) in anhydrous THF (10 mL) was added trimethyl borate (0.80 mL, 7.1 mmol) at RT. The resulting mixture was stirred for 15 min, then cooled in an ice bath and treated with borane-dimethyl sulfide (6.4 mL of 2.0 M solution in THF, 12.8 mmol) slowly. The reaction mixture was stirred for 4 h at RT. Methanol (0.5 mL) was added dropwise at RT. After stirring for 30 min, the reaction mixture was concentrated under vacuum. The residue was diluted with of ethyl acetate, washed with a saturated aqueous solution of sodium bicarbonate followed by brine. The resulting organic solution was then dried over magnesium sulfate and concentrated under reduced pressure to give 2-fluoro-3-iodo-4-methylphenyl)methanol as an off-white amorphous solid, which was used without further purification.

1. temperaturecooled in an ice bath
2. stirringThe reaction mixture was stirred for 4 h at RT
3. stirringAfter stirring for 30 min
4. concentrationthe reaction mixture was concentrated under vacuum
5. additionThe residue was diluted with of ethyl acetate
6. washwashed with a saturated aqueous solution of sodium bicarbonate
7. dry with materialThe resulting organic solution was then dried over magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customto give 2-fluoro-3-iodo-4-methylphenyl)methanol as an off-white amorphous solid, which
10. customwas used without further purification

ORD record

ord-dea0b090aabd4dcd9f669dae84e2f1bf

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07759337B2