Phosphorus pentabromide → Ethyl alpha-bromo-gamma-(2'-chloro-4-biphenylyl)butyrate

HRID 1659081Notes

Reaction equation

HRID 1659081 reaction equation
O[CH:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].P(Br)(Br)(Br)(Br)[Br:24]>>[Br:24][CH:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

3

Reactant 2

HCID 62678Phosphorus pentabromideHCID 21526346Ethyl alpha-hydroxy-gamma-(2'-chloro-4-biphenylyl)butyrate

Product 1

HCID 21526579Ethyl alpha-bromo-gamma-(2'-chloro-4-biphenylyl)butyrate

Procedure

To 15.4 g. (0.0476 moles) of ethyl α-hydroxy-γ-(2'-chloro-4-biphenylyl)butyrate there is added slowly with stirring at 40°-50°C 23 g. (0.053 moles) of phosphorus pentabromide. The mixture is stirred at room temperature for 16 hours, then diluted with 70 ml. of petroleum ether, and poured into 125 ml. of ice-cold water. The organic phase is separated, washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, filtered and the solvent removed in vacuo to obtain ethyl α-bromo-γ-(2'-chloro-4-biphenylyl)butyrate.

Workup

  1. stirringThe mixture is stirred at room temperature for 16 hours
  2. additiondiluted with 70 ml
  3. customThe organic phase is separated
  4. washwashed with saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-e128852de38c4bb18ae598028f7b78dc
Source dataset
uspto-grants-1976_06
Patent number
US03966801

Reaction notes

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