Hydrogen Bromide → HCID 19934844, compound

HRID 37240Notes

Reaction equation

HRID 37240 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-388e39c0bd954c25bb138926dc253b06
Source dataset
uspto-grants-1995_05
Patent number
US05420133

Reaction notes

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