Phosphorus pentabromide → Ethyl alpha-bromo-3-chloro-4-cyclohexylphenylacetate

HRID 436318Notes

Reaction equation

HRID 436318 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14](O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[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:22]>>[Br:22][CH: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:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

3

Reactant 2

HCID 62678Phosphorus pentabromideHCID 21454168HCID 21454168, compound

Product 1

HCID 21454151Ethyl alpha-bromo-3-chloro-4-cyclohexylphenylacetate

Procedure

To 15.0 g. (0.0476 moles) of ethyl 3-chloro-4-cyclohexylphenylglycolate 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-3-chloro-4-cyclohexylphenylacetate.

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-678e253d7daf454d86509417b794d6e3
Source dataset
uspto-grants-1977_02
Patent number
US04008269

Reaction notes

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