(Triphenylphosphoranylidene)acetonitrile → HCID 15155558, compound

HRID 2396703Notes

Reaction equation

HRID 2396703 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][C:7](=O)[C:6]=2[CH:11]=1.[C:12]([CH:14]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:13].[PH5]>C1(C)C(C)=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[C:7]([CH2:14][C:12]#[N:13])[C:6]=2[CH:11]=1

Participants

5

Reactant 3

HCID 85524(Triphenylphosphoranylidene)acetonitrileHCID 105127485-Bromobenzo[b]furan-3(2H)-oneHCID 178527699HCID 178527699, compound

Product 1

HCID 15155558HCID 15155558, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A suspension of 5-bromo-3-(2H)-benzofuranone (4.26 g) and cyanomethylene triphenylphosphorane (9.06 g) in dry xylene (100 ml) was heated at reflux for 24 h . A further quantity of the phosphorane (450 mg) was added and heating continued for a further period of 12 h. On cooling to ambient temperature the brown coloured suspension was evaporated to dryness in vacuo. Chromatography of the residue using dichloromethane:hexane (1:3) as eluant afforded a cream coloured product. Recrystallization (from ethanol) of the chromatographed material afforded the title compound as cream flakes, m.p. 120°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. temperatureheating
  4. customwas evaporated to dryness in vacuo
  5. customafforded a cream coloured product
  6. customRecrystallization (from ethanol) of the chromatographed material

Sources & evidence

ORD record
ord-c4fdb7cb903143828b878dc1dce80776
Source dataset
uspto-grants-1996_02
Patent number
US05494910

Reaction notes

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