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

HRID 1765433Notes

Reaction equation

HRID 1765433 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-3d1162074ad74fdba01b2d69d8966ce5
Source dataset
uspto-grants-2007_06
Patent number
US07226940B2

Reaction notes

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