Hydrogen Peroxide → 2-(3-Bromophenyl)ethan-1-ol

HRID 1107719Notes

Reaction equation

HRID 1107719 reaction equation
B.CSC.[Br:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[CH2:10].[OH-:14].[Na+].OO>C1COCC1.O>[Br:5][C:6]1[CH:7]=[C:8]([CH2:9][CH2:10][OH:14])[CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 748703-BromostyreneHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 27340902-(3-Bromophenyl)ethan-1-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Borane-dimethylsulphide complex (2.0M in THF, 49 ml) was added dropwise to a stirred solution of 3-bromostyrene (10 g, 55 mmol) in THF (130 ml) at 0° C. and the solution was stirred for 3 h at room temperature. 10% Aqueous sodium hydroxide was added cautiously, followed by hydrogen peroxide (30% wt. solution in water, 6 ml) dropwise. After a further 16 h, the mixture was diluted with water, extracted twice with ethyl acetate, the combined extracts washed with saturated sodium bisulphite solution and saturated sodium chloride solution, dried over sodium sulphate and evaporated to give a colourless oil. Purification by flash chromatography, eluting with 30% diethyl ether/hexane gave a colourless oil, [M+Si(CH3)3 derivative]+ 272.

Workup

  1. waitAfter a further 16 h
  2. extractionextracted twice with ethyl acetate
  3. washthe combined extracts washed with saturated sodium bisulphite solution and saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customto give a colourless oil
  7. customPurification by flash chromatography
  8. washeluting with 30% diethyl ether/hexane
  9. customgave a colourless oil

Sources & evidence

ORD record
ord-0346461a71174ad098f117cb200b1dfd
Source dataset
uspto-grants-2000_05
Patent number
US06063789

Reaction notes

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