Hydrochloric Acid → (5-Bromo-2-methylphenyl)methanol

HRID 1391732Notes

Reaction equation

HRID 1391732 reaction equation
B.[Br:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:12])=[C:7]([CH:11]=1)[C:8](O)=[O:9].CO.Cl>C1COCC1>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:12])=[C:7]([CH2:8][OH:9])[CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6331BoraneHCID 3460045-Bromo-2-methylbenzoic acid

Product 1

HCID 12993770(5-Bromo-2-methylphenyl)methanolYield 82.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Borane (10.80 mL of a 1M solution in THF, 10.80 mmol) was added to a cooled solution of 5-bromo-2-methyl-benzoic acid (116 mg, 0.54 mmol) in THF (15 mL), under nitrogen, at 0° C. (ice water bath) and the resulting mixture allowed to warm to rt overnight. The mixture was then treated with MeOH (10 mL) followed by aqueous HCl (2M, 20 mL) and the mixture stirred for about 15 minutes, concentrated under vacuum and then partitioned with EtOAc. The organic layer was washed with aqueous HCl (2M), water and brine, dried (MgSO4), filtered and reduced to give the title compound as a colourless oil (90 mg).

Workup

  1. concentrationconcentrated under vacuum
  2. custompartitioned with EtOAc
  3. washThe organic layer was washed with aqueous HCl (2M), water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-c19a3a27349e43f38b00742632c0e985
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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