Hydrogen Bromide → HCID 19934844, compound

HRID 274924Notes

Reaction equation

HRID 274924 reaction equation
[CH2:1]([C:4]1[CH:23]=[C:22]([CH2:24]O)[CH:21]=[C:20]([CH2:26][CH2:27][CH3:28])[C:5]=1[O:6][CH:7]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:2][CH3:3].P(Br)(Br)[Br:30].Br>C(Cl)(Cl)(Cl)Cl>[CH2:1]([C:4]1[CH:23]=[C:22]([CH2:24][Br:30])[CH:21]=[C:20]([CH2:26][CH2:27][CH3:28])[C:5]=1[O:6][CH:7]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24614Phosphorus tribromideHCID 19934840HCID 19934840, compound

Product 1

HCID 19934844HCID 19934844, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2.03 g (5.29 mmol) of the product of Step B dissolved in 10 mL of carbon tetrachloride was added 0.50 mL (5.29 mmol) of phosphorous tribromide and the reaction mixture was magnetically stirred at room temperature for 1 hour as hydrogen bromide was evolved. The magnetic stir bar was removed, and the reaction mixture was concentrated in vacuo. The residue was redissolved and evaporated from methylene chloride three times to remove most of the hydrogen bromide. Finally, the residue was purified by rapid flash chromatography on a silica gel column eluted with 20% EtOAc-hexane. Combination and evaporation of the purified fractions in vacuo afforded 2.27 (96%) of the title compound.

Workup

  1. customThe magnetic stir bar was removed
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was redissolved
  4. customevaporated from methylene chloride three times
  5. customto remove most of the hydrogen bromide
  6. customFinally, the residue was purified by rapid flash chromatography on a silica gel column
  7. washeluted with 20% EtOAc-hexane
  8. customCombination and evaporation of the purified fractions in vacuo

Sources & evidence

ORD record
ord-a77222d4b94a4f4eba60a71cc6484a1f
Source dataset
uspto-grants-1995_02
Patent number
US05391566

Reaction notes

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