4-Iodo-3-methylbenzoic acid → (4-Iodo-3-methylphenyl)methanol

To a solution of 4-iodo-3-methyl-benzoic acid (5.2 g, 20 mmol) in THF (30 mL), is added 2.0 M borane-dimethyl sulfide complex in THF (40.0 mL, 80 mmol) dropwise. The reaction mixture is stirred overnight. The reaction mixture is quenched carefully at 0° C. with methanol (20 mL) and the mixture is evaporated to dryness under reduced pressure. The residue is partitioned between EtOAc (80 mL) and water (60 mL). The organic phase is washed with brine (60 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to a residue. The residue is purified by flash chromatography (AnaLogix, gradient EtOAc/Hexane) to give (4-Iodo-3-methyl-phenyl)-methanol as white solid (4.7 g, 95%). 1HNMR (CDCl3) (ppm): 2.4 (3H, s), 4.55 (2H, s), 6.8-7.75 (3H, m).

1. customThe reaction mixture is quenched carefully at 0° C. with methanol (20 mL)
2. customthe mixture is evaporated to dryness under reduced pressure
3. customThe residue is partitioned between EtOAc (80 mL) and water (60 mL)
4. washThe organic phase is washed with brine (60 mL)
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure to a residue
8. customThe residue is purified by flash chromatography (AnaLogix, gradient EtOAc/Hexane)

ORD record

ord-c972eae0d6c14fa291d1d2d6dbb11997

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08106077B2