Water → HCID 14497613, compound

HRID 1086227Notes

Reaction equation

HRID 1086227 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[CH:11]\[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])/[CH2:9]O)=[CH:4][CH:3]=1.N1C=CC=CC=1.P(Br)(Br)[Br:26].O>C(OC)(C)(C)C>[Br:26][CH2:9]/[C:8](/[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[CH:11]/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24614Phosphorus tribromideHCID 14497611HCID 14497611, compound

Product 1

HCID 14497613HCID 14497613, compoundYield 236%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

103.1 g of E-2-(4-fluorophenyl)-3-(2-chlorophenyl)-prop-2-enol are dissolved in 700 ml of methyl tert-butyl ether, and 2 ml of pyridine are added. The reaction solution is stirred under a nitrogen atmosphere at 0° C., while 27.2 g of phosphorus tribromide are added in the course of 90 minutes. After the end of the addition, the mixture is refluxed for two hours and then poured onto 500 ml of water and extracted several times with methyl tert-butyl ether. The organic phase is washed with sodium bicarbonate solution and water and dried over sodium sulfate, and the solvent is evaporated down under reduced pressure. 77.2 g (61%) of E-1-bromo-2-(4-fluorophenyl)-3-(2-chlorophenyl)-prop-2-ene of melting point 68° C. are obtained from ethanol.

Workup

  1. additionare added in the course of 90 minutes
  2. additionAfter the end of the addition
  3. temperaturethe mixture is refluxed for two hours
  4. extractionextracted several times with methyl tert-butyl ether
  5. washThe organic phase is washed with sodium bicarbonate solution and water
  6. dry with materialdried over sodium sulfate
  7. customthe solvent is evaporated down under reduced pressure

Sources & evidence

ORD record
ord-b2dc2e4c2a0b40a2805c799d8e1f1c91
Source dataset
uspto-grants-1991_07
Patent number
US05028618

Reaction notes

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