Phosphorus tribromide → HCID 19934843, compound

HRID 37243Notes

Reaction equation

HRID 37243 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>[CH3:1][C:2]1[CH:20]=[C:19]([CH2:21][Br:25])[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]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 19934850HCID 19934850, compound

Product 1

HCID 19934843HCID 19934843, compoundYield 82.2%

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 mL of carbon tetrachloride was added 0.154 mL (1.6 mmol) of phosphorous tribromide and the reaction mixture was stirred at room temperature for 15 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-6342ed4fab154e13931b420ac5664ff3
Source dataset
uspto-grants-1995_05
Patent number
US05420133

Reaction notes

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