(3-Bromophenyl)acetic acid → 2-(3-Bromophenyl)ethan-1-ol

HRID 517529Notes

Reaction equation

HRID 517529 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.C1COCC1>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 74653(3-Bromophenyl)acetic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 27340902-(3-Bromophenyl)ethan-1-olYield 97.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-bromophenyl)acetic acid (10.0 g, 0.046 mol) in THF (150 mL), 1 M BH3-THF (100 mL, 100 mmol) was dropwise added at RT. The mixture was stirred overnight, concentrated, diluted with H2O (100 mL), and extracted with EtOAc (100 m×3). The combined organic layers were washed with H2O and brine, dried over Na2SO4, filtered, and concentrated to afford the crude product 2-(3-bromophenyl)ethanol (9.0 g, 97%) as a colorless oil, which was directly used for next step without further purification. MS (ES+) C8H9BrO requires: 200, 202 found: 201 [M+H]+, 203 [M+2+H]+(1:1).

Workup

  1. concentrationconcentrated
  2. additiondiluted with H2O (100 mL)
  3. extractionextracted with EtOAc (100 m×3)
  4. washThe combined organic layers were washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e687f242b1b744869b0c93574cf05510
Source dataset
uspto-grants-2015_08
Patent number
US09115120B2

Reaction notes

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