3-Bromo-2-methylbenzoic Acid → (3-Bromo-2-methylphenyl)methanol

HRID 1848402Notes

Reaction equation

HRID 1848402 reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6]>C1COCC1>[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([CH2:5][OH:6])[CH:8]=[CH:9][CH:10]=1

Participants

3

Reactant 1

HCID 27355903-Bromo-2-methylbenzoic Acid

Product 1

HCID 10035697(3-Bromo-2-methylphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-2-methyl benzoic acid (35 g, 163 mmol) in THF (200 mL) was added Borane THF Complex (1.0 M, 212 mL, 212 mmol). The mixture was allowed to stir for 24 h. TLC showed one single product spot. The reaction was quenched with water. The solvent THF was removed under reduced pressure. The resulting solid was dissolved in ethyl acetate (500 mL), washed with 1N HCl, sodium carbonate, and brine. The organic layer was dried over sodium sulfate and concentrated to afford (3-bromo-2-methylphenyl)methanol. 1H NMR (500 MHz, CDCl3) δ 7.76 (d, J=8.0 Hz, 1H), 7.63 (d, J=8.0 Hz, 1H), 5.30 (s, 2H), 2.42 (s, 3H).

Workup

  1. customThe reaction was quenched with water
  2. customThe solvent THF was removed under reduced pressure
  3. dissolutionThe resulting solid was dissolved in ethyl acetate (500 mL)
  4. washwashed with 1N HCl, sodium carbonate, and brine
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1a40f424919d421f8d8410651ccd4448
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

Loading…