Phosphine, triphenyl-, hydrobromide → 5-bromo-1-methylene-2,3-dihydro-1H-indene

HRID 855311Notes

Reaction equation

HRID 855311 reaction equation
[Br-].[C:2]1([PH+](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Li]CCCC.[Br:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[C:32](=O)[CH2:31][CH2:30]2>CS(C)=O>[Br:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[C:32](=[CH2:2])[CH2:31][CH2:30]2

Participants

5

Reactant 3

HCID 517696Phosphine, triphenyl-, hydrobromideHCID 5206955-Bromo-1-indanoneHCID 178418339Butyllithium

Product 1

HCID 588409305-bromo-1-methylene-2,3-dihydro-1H-indeneYield 59%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was synthesized in analogy to example S87 using triphenyl-phospho-nium bromide (1.49 g, 4.17 mmol), n-BuLi (3.26 ml, 1.6M solution in hexane, 5.21 mmol) and 5-bromo-1-indanone (880 mg, 4.17 mmol) in DMSO (10 ml). The residue which was isolated was purified by filtration through a short pad of silica using pentane as eluant to give 5-bromo-1-methylene-indan (510 mg, 59%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ 7.40-7.29 (m, 3H), 5.44 (m, 1H), 5.05 (m, 1H), 2.98-2.94 (m, 2H), 2.83-2.78 (m, 2H).

Workup

  1. customThe residue which was isolated
  2. filtrationwas purified by filtration through a short pad of silica

Sources & evidence

ORD record
ord-54710dbaaa7d4ffba68120c6463a6a25
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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