Triphenylphosphine dibromide → HCID 19815611, compound

HRID 466193Notes

Reaction equation

HRID 466193 reaction equation
O[CH2:2][CH:3]1[CH2:8][C:7]2[CH:9]=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:6]=2[S:5][CH2:4]1.[Br:15]P(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(#N)C>[Br:15][CH2:2][CH:3]1[CH2:8][C:7]2[CH:9]=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:6]=2[S:5][CH2:4]1

Participants

4

Reactant 2

HCID 70579Triphenylphosphine dibromideHCID 19815618HCID 19815618, compound

Product 1

HCID 19815611HCID 19815611, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The alcohol (3.43 g, 16.31 mmol) is dissolved in 150 ml of acetonitrile and treated with dibromotriphenylphosphorane (6.88 g, 16.31 mmol). The solvent is removed in vacuo, and the residue is triturated with ether. The solid is removed by filtration and washed with ether. The ether solution is concentrated and the residue is chromatographed (silica gel, 20% EtOAc/hexane) to give 3-bromomethyl-6-methoxy-3,4-dihydro-2H-1-benzothiopyran as an oil.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is triturated with ether
  3. customThe solid is removed by filtration
  4. washwashed with ether
  5. concentrationThe ether solution is concentrated
  6. customthe residue is chromatographed (silica gel, 20% EtOAc/hexane)

Sources & evidence

ORD record
ord-c92f1478bbac433fb96a77a68d78fd26
Source dataset
uspto-grants-1992_10
Patent number
US05155130

Reaction notes

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