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

HRID 14977

Reaction equation

HRID 14977 reaction equation
C([C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[C:5]([CH3:12])[C:4]=1[Br:13])C.CO.Cl>O1CCCC1>[Br:13][C:4]1[C:5]([CH3:12])=[C:6]([CH2:7][OH:8])[CH:10]=[CH:11][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 67045088Ethyl 3-bromo-2-methylbenzoic acid2×

Product 1

HCID 10035697(3-Bromo-2-methylphenyl)methanolYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-bromo-2-methylbenzoic acid was reduced as follows: Add 5 equivalents of borane tetrahydrofuran complex, via syringe, to 10 mmol ethyl 3-bromo-2-methylbenzoic acid in tetrahydrofuran (5 mL). The mixture was refluxed for two hours, then cooled in an ice bath. Methanol (10 mL) was added dropwise, followed by 1 N HCl (50 mL). The solvent was removed and the mixture partitioned between ethyl acetate and water. The yield was 90%. 1H NMR (Varian 300 MHz, CDCl3, shifts relative to the solvent peak at 7.24 ppm) 67.5 (d, 1H) 7.2 (d, 1H) 7.1 (t, 1H), 4.6 (s, 2H) 2.3 (s, 3H).

Workup

  1. additionAdd 5 equivalents of borane tetrahydrofuran complex
  2. temperatureThe mixture was refluxed for two hours
  3. temperaturecooled in an ice bath
  4. customThe solvent was removed
  5. customthe mixture partitioned between ethyl acetate and water

Sources & evidence

ORD record
ord-1c31d44872d04c0c869ef0842a3a3eab
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Linked notes

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