Water → 2-(3-Bromophenyl)ethan-1-ol

HRID 429361Notes

Reaction equation

HRID 429361 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9](O)=[O:10])[CH:5]=[CH:6][CH:7]=1.B#B.O>O1CCCC1>[OH:10][CH2:9][CH2:8][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 74653(3-Bromophenyl)acetic acidHCID 6328200Diboron

Product 1

HCID 27340902-(3-Bromophenyl)ethan-1-olYield 96.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromophenylacetic acid (10 g, 46.5 mmol) in tetrahydrofuran (100 ml) at 0° C. was added diborane (70 ml, 1.0 M solution in tetrahydrofuran). The reaction mixture was allowed to warm to room temperature. After 16 h, the reaction mixture was cooled to 0°C. and water was added dropwise (50 ml). The organic layer was separated and washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (elution gradient: 40-60% ethyl acetate/hexane) to give 3-(2-hydroxyethyl)bromobenzene (9.0 g).

Workup

  1. temperaturethe reaction mixture was cooled to 0°C.
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (elution gradient: 40-60% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2c5b3bab97b5422b9345e3bdd5705d3b
Source dataset
uspto-grants-2001_11
Patent number
US06316466B1

Reaction notes

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