Phosphorus pentabromide → HCID 21506232, compound

HRID 1287680Notes

Reaction equation

HRID 1287680 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:14][CH:15](O)[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.P(Br)(Br)(Br)(Br)[Br:23]>>[Br:23][CH:15]([CH2:14][C:4]1[CH:5]=[CH:6][C:7]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[C:2]([Cl:1])[CH:3]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

3

Reactant 2

HCID 62678Phosphorus pentabromideHCID 21506243HCID 21506243, compound

Product 1

HCID 21506232HCID 21506232, compound

Procedure

To 15.6 g. (0.0476 moles) of ethyl β-(3-chloro-4-cyclohexylphenyl)lactate 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-β-(3-chloro-4-cyclohexylphenyl)propionate.

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-dd017f79484241acb45a55aee5d57352
Source dataset
uspto-grants-1976_10
Patent number
US03985788

Reaction notes

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