Triphenylphosphine dibromide → 1-(4-(Bromomethyl)phenyl)propan-2-one

HRID 434368Notes

Reaction equation

HRID 434368 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[O:12])[CH3:11])=[CH:5][CH:4]=1.[Br:13]P(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(#N)C>[Br:13][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[O:12])[CH3:11])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 70579Triphenylphosphine dibromideHCID 204938341-[4-(Hydroxymethyl)phenyl]propan-2-one

Product 1

HCID 198744891-(4-(Bromomethyl)phenyl)propan-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(4-hydroxymethylphenyl)propan-2-one (3.15 g) and dibromotriphenylphosphorane (8.11 g) was refluxed in acetonitrile (50 ml) for 1 hour. The solvent was removed and the residue chromatographed on silica. Elution with ether gave 1-(4-bromomethylphenyl)propan-2-one, 3.4 g. τ(CDCl3) 7.92 (3H, s), 6.4 (2H, s), 5.6 (2H, s), 2.9 (2H, d, J=8 Hz), 2.65 (2H, d, J=8 Hz). This was ketalised in an analogous manner to that described in Description 2 to give the title compound, 3.73 g. τ(CDCl3) 8.7 (3H, s), 7.1 (2H, s), 5.9-6.3 (4H, m), 5.54 (2H, s), 2.75 (4H, s).

Workup

  1. customThe solvent was removed
  2. customthe residue chromatographed on silica
  3. washElution with ether

Sources & evidence

ORD record
ord-e14579ec33bb4ce6aeceaba45bdced14
Source dataset
uspto-grants-1983_08
Patent number
US04396627

Reaction notes

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