Triphenylphosphine dibromide → HCID 14971319, compound

HRID 466173Notes

Reaction equation

HRID 466173 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C:9]([CH2:12]O)=[CH:8][C:7]=2[CH:14]=1.[Br:15]P(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C:9]([CH2:12][Br:15])=[CH:8][C:7]=2[CH:14]=1

Participants

4

Reactant 2

HCID 70579Triphenylphosphine dibromideHCID 13601222HCID 13601222, compound

Product 1

HCID 14971319HCID 14971319, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-Methoxy-3-(hydroxymethyl)-2H-1-benzopyran (4.35 g, 22.6 mmol) is dissolved in 70 ml of dry acetonitrile and treated with dibromotriphenylphosphorane (9.56 g, 22.6 mmol). After 15 min, the mixture is evaporated in vacuo. The residue is triturated with 100 ml of an ether/hexane mixture (1:1). The solid is removed by filtration (medium frit) and washed with several 50 ml portions of the ether/hexane mixture. The organic extracts are combined and evaporated to give 6-methoxy-3-(bromomethyl)-2H-1-benzopyran which is used without any further purification.

Workup

  1. customthe mixture is evaporated in vacuo
  2. customThe residue is triturated with 100 ml of an ether/hexane mixture (1:1)
  3. customThe solid is removed by filtration (medium frit)
  4. washwashed with several 50 ml portions of the ether/hexane mixture
  5. customevaporated

Sources & evidence

ORD record
ord-d98e93658c5549a4a6365e494319f82a
Source dataset
uspto-grants-1992_10
Patent number
US05155130

Reaction notes

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