Methyl 4-bromo-3-methylbenzoate → (4-Bromo-3-methylphenyl)methanol

HRID 1750756Notes

Reaction equation

HRID 1750756 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[CH:4][C:3]=1[CH3:12].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[CH3:12]

Participants

4

Reactant 2

HCID 3294148Methyl 4-bromo-3-methylbenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 10987288(4-Bromo-3-methylphenyl)methanolYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-bromo-3-methylbenzoate (500 mg, 2.18 mmol) in THF (5.2 mL) at −30° C. was slowly added LiAlH4 (83 mg, 2.18 mmol). The reaction mixture was stirred for 15 min, quenched with a solution of methanol and water (4:1, 10 mL), and stirred at rt for 30 min. The mixture was neutralized with 6 N HCl to pH of 7 and extracted with ethyl acetate (20 mL). The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to afford (4-bromo-3-methylphenyl)methanol (420 mg; yield 96%) as an oil.

Workup

  1. customat −30° C.
  2. customquenched with a solution of methanol and water (4:1, 10 mL)
  3. stirringstirred at rt for 30 min
  4. extractionextracted with ethyl acetate (20 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-988f72b5604e4667ae9dcad1ed5ee7a1
Source dataset
uspto-grants-2015_10
Patent number
US09156860B2

Reaction notes

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