Triphenylphosphine → 1-(p-Chlorophenyl)-1-(3-bromo-2-fluoropropenyl)cyclopropane

HRID 1385643Notes

Reaction equation

HRID 1385643 reaction equation
[Br:1]Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2([CH:32]=[C:33]([F:36])[CH2:34]O)[CH2:31][CH2:30]2)=[CH:25][CH:24]=1>C(Cl)(Cl)(Cl)Cl>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2([CH:32]=[C:33]([F:36])[CH2:34][Br:1])[CH2:31][CH2:30]2)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24408BromineHCID 543549731-(4-Chlorophenyl)-1-(2-fluoro-3-hydroxyprop-1-enyl) cyclopropane

Product 1

HCID 537657641-(p-Chlorophenyl)-1-(3-bromo-2-fluoropropenyl)cyclopropaneYield 63%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent3×

Procedure

Under a nitrogen atmosphere, a solution of bromine (0.767 g, 4.8 mmol) in carbon tetrachloride at ice-water bath temperature is treated sequentially with a solution of triphenylphosphine (1.26 g, 4.8 mmol) in carbon tetrachloride and a solution of 3-[1-(p-chlorophenyl)-cyclopropyl]-2-fluoro-2-propen-1-ol, (Z)—(0.907 g, 4 mmol) in carbon tetrachloride, heated to and stirred at reflux for 70 minutes, cooled to room temperature, and poured into petroleum ether. The resultant mixture is filtered, and the filtrate is concentrated in vacuo to obtain a residue. The residue is dissolved in petroleum ether and passed through a plug of silica gel (eluted with hexanes) to obtain an oil. Flash column chromatography of the oil using silica gel and a 3:20 methylene chloride/hexanes solution gives the title product as a colorless oil (0.73 g, 63% yield) which is identified by NMR spectral analyses.

Workup

  1. temperatureat reflux for 70 minutes
  2. filtrationThe resultant mixture is filtered
  3. concentrationthe filtrate is concentrated in vacuo
  4. customto obtain a residue
  5. customto obtain an oil

Sources & evidence

ORD record
ord-b051a02e5b6d4031a2147734b6c2ffb3
Source dataset
uspto-grants-2001_07
Patent number
US06262319B1

Reaction notes

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