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

HRID 2386576Notes

Reaction equation

HRID 2386576 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) δ7.5 (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-b740a9ca83424e70bc7bcf03340d4eb9
Source dataset
uspto-grants-2012_09
Patent number
US08268822B2

Reaction notes

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