Ethyl Acetate → 2-(4-Bromophenyl)butan-1-ol

HRID 735694Notes

Reaction equation

HRID 735694 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12][CH3:13])[C:9](O)=[O:10])=[CH:4][CH:3]=1.CCOC(C)=O>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:12][CH3:13])[CH2:9][OH:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 574722-(4-Bromophenyl)butanoic acid

Product 1

HCID 578429142-(4-Bromophenyl)butan-1-olYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 75B (96 mg, 0.4 mmol) in 3 mL THF was added BH3 (2M in THF, 0.5 mL, 1 mmol). The solution was stirred at rt for 16 h. EtOAc (20 mL) was added, and the organic phase washed with 1M H3PO4, sat. NaHCO3 and brine, dried (Na2SO4), and concentrated. Purification via flash chromatography (0-30% EtOAc in hexanes) gives 75C (86 mg, 96%). MS (ESI) m/z 211.2(M−H2O)+.

Workup

  1. washthe organic phase washed with 1M H3PO4, sat. NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customPurification via flash chromatography (0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-331f3055c50e409397c439801d9504f2
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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