Methanol → 1-Bromo-4-phenylbutane

HRID 1068131Notes

Reaction equation

HRID 1068131 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br-:12].[Br-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO>C(#N)C>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][Br:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 76889BenzenebutanolHCID 12890784Triphenylphosphane dibromide

Product 1

HCID 2596681-Bromo-4-phenylbutaneYield 106.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-phenyl-1-butanol (21.75 g) in acetonitrile (300 mL) was added triphenylphosphine dibromide (67.23 g) in portions with stirring over 10 min. After stirring over night under nitrogen, methanol (4 mL) was added and after 1.5 h, the solvent was removed under reduced pressure. Hexanes (200 mL) and ˜75 g silica gel were added to the residue and the mixture was filtered and the filter cake was eluted with hexanes. The clear filtrate was concentrated to give 32.8 g of clear colorless liquid. This product was again eluted through silica gel using 1.5 L hexanes to give the title compound (24.7 g) as a colorless liquid. 1H NMR (500 MHz, CDCl3): δ7.28-7.32 (m, 2 H), 7.20-7.23 (m, 3 H), 3.44 (t, J=6.8 Hz, 2 H), 2.67 (t, J =7.6 Hz, 2 H), 1.93-1.89 (m, 2 H), 1.77-1.84 (m, 2 H).

Workup

  1. stirringAfter stirring over night under nitrogen
  2. customthe solvent was removed under reduced pressure
  3. additionHexanes (200 mL) and ˜75 g silica gel were added to the residue
  4. filtrationthe mixture was filtered
  5. washthe filter cake was eluted with hexanes
  6. concentrationThe clear filtrate was concentrated

Sources & evidence

ORD record
ord-c2e011dfa1744476b3a8c7acdfdea3e0
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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