Phosphorus pentabromide → Ethyl alpha-bromo-2'-chloro-4-biphenylylacetate

HRID 267388

Reaction equation

HRID 267388 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14](O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10][CH:9]=1.P(Br)(Br)(Br)(Br)[Br:22]>>[Br:22][CH:14]([C:11]1[CH:12]=[CH:13][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[CH:9][CH:10]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

3

Reactant 2

HCID 62678Phosphorus pentabromideHCID 21556089Ethyl 2'-chloro-4-biphenylylglycolate

Product 1

HCID 21556258Ethyl alpha-bromo-2'-chloro-4-biphenylylacetate

Procedure

To 15.0 g. (0.0476 moles) of ethyl 2'-chloro-4-biphenylylglycolate 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-2'-chloro-4-biphenylylacetate.

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-972bcdda42be47e491f931bf35cb1fed
Source dataset
uspto-grants-1976_03
Patent number
US03941821

Linked notes

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