Borane;tetrahydrofuran → HCID 66643901, compound

HRID 1474334Notes

Reaction equation

HRID 1474334 reaction equation
[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[C:5](O)=[O:6].B.C1COCC1>C1COCC1>[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([CH2:5][OH:6])[CH:8]=[C:9]([F:11])[CH:10]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 666439353-bromo-5-fluoro-2-methylbenzoic acid

Product 1

HCID 66643901HCID 66643901, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of 3-bromo-5-fluoro-2-methyl-benzoic acid (3 g, 12.9 mmol) in dry THF (20 mL) was added borane THF complex (25.8 mL, 1 M in THF, 25.8 mmol) slowly. The resulting mixture was stirred at room temperature overnight, then quenched with MeOH and concentrated. The residue was purified by column chromatography to give (3-bromo-5-fluoro-2-methyl-phenyl)-methanol. 1H-NMR (400 MHz, CDCl3) δ ppm 7.25 (dd, J=8.6 Hz, J=3.1 Hz, 1H), 7.15 (dd, J=8.6 Hz, J=2.3 Hz, 1H), 4.71 (s, 2H), 2.33 (s, 3H).

Workup

  1. customquenched with MeOH
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-fb84c47aee3546308b1b0a10645d098f
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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