Phosphorus tribromide → HCID 19934843, compound

HRID 1492646Notes

Reaction equation

HRID 1492646 reaction equation
[CH3:1][C:2]1[CH:20]=[C:19]([CH2:21]O)[CH:18]=[C:17]([CH3:23])[C:3]=1[O:4][CH:5]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=1)[C:6]([O:8][CH3:9])=[O:7].P(Br)(Br)[Br:25]>C(Cl)(Cl)(Cl)Cl>[Br:25][CH2:21][C:19]1[CH:20]=[C:2]([CH3:1])[C:3]([O:4][CH:5]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C:6]([O:8][CH3:9])=[O:7])=[C:17]([CH3:23])[CH:18]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 19934850HCID 19934850, compound

Product 1

HCID 19934843HCID 19934843, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 0.560 g (1.62 mmol) of the product of Step B dissolved in 5.0 mL of carbon tetrachloride was added 154 μL (1.62 mmol) of phosphorous tribromide and the reaction mixture was stirred at room temperature for 5 minutes. Carbon tetrachloride was evaporated from the reaction mixture several times to remove the hydrogen bromide, then the residue was purified on a silica gel flash chromatography column eluted with 5% EtOAc-hexane. The purified fractions were evaporated in vacuo affording 0.523 g (81%) of the title compound.

Workup

  1. customCarbon tetrachloride was evaporated from the reaction mixture several times
  2. customto remove the hydrogen bromide
  3. customthe residue was purified on a silica gel flash chromatography column
  4. washeluted with 5% EtOAc-hexane
  5. customThe purified fractions were evaporated in vacuo

Sources & evidence

ORD record
ord-f3cf0c7726ae4a7495c91f8f2ebf088b
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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