Methanol → (3-Bromo-4-chlorophenyl)methanol

HRID 488841Notes

Reaction equation

HRID 488841 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Br:12])[CH:6]=1)C.[H-].C([Al+]CC(C)C)C(C)C.CO.O>C1(C)C=CC=CC=1>[Br:12][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[Cl:11])[CH2:4][OH:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 12594300Ethyl 3-bromo-4-chlorobenzoateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 50998689(3-Bromo-4-chlorophenyl)methanolYield 99.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of ethyl-3-bromo-4-chlorobenzoate (3.25 g, 12.34 mmol) in toluene (70 mL) was added, at −78° C. under argon, diisobutylaluminum hydride (1.5M in toluene, 24 mL, 37.01 mmol). The reaction mixture was stirred at −78° C. for 1 hr then methanol (9 mL) and water (18 mL) was added. The solution was warmed up to room temperature and extracted with ethyl acetate. The organic layer was washed successively with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated to give 2.73 g of 3-bromo-4-chloro-benzyl alcohol.

Workup

  1. temperatureThe solution was warmed up to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed successively with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-4ec6851a0f984595b5354a846da21dc5
Source dataset
uspto-grants-2005_12
Patent number
US06974826B2

Reaction notes

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