Triphenylphosphine → 1-Bromo-4-(p-chlorophenyl)-3-fluoro-4-methyl-2-pentene

HRID 1977709Notes

Reaction equation

HRID 1977709 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([CH3:36])([CH3:35])[C:30]([F:34])=[CH:31][CH2:32]O)=[CH:25][CH:24]=1.C(OCC)(=O)C.CCCCCC>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:32][CH:31]=[C:30]([F:34])[C:29]([C:26]1[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=1)([CH3:36])[CH3:35]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 24408BromineHCID 21226206Ethyl acetate hexaneHCID 545663494-(p-Chlorophenyl)-3-fluoro-4-methyl-2-penten-1-ol

Product 1

HCID 542729131-Bromo-4-(p-chlorophenyl)-3-fluoro-4-methyl-2-penteneYield 92.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent3×

Procedure

A solution of triphenyl phosphine (12.58 g, 55.6 mmol) in carbon tetrachloride at −5° C. to 5° C. is treated dropwise with a solution of bromine (8.89 g, 55.6 mmol) in carbon tetrachloride over 50 minutes under nitrogen, stirred at room temperature for one hour, treated with a solution of 4-(p-chlorophenyl)-3-fluoro-4-methyl-2-penten-1-ol, (Z)- (10.6 g, 46.3 mmol) in carbon tetrachloride over 15 minutes, refluxed for 2.5 hours, cooled to room temperature, and poured into petroleum ether. The resultant mixture is filtered through diatomaceous earth and concentrated in vacuo to obtain a residue. Flash chromatography of the residue using silica gel and a 1:9 ethyl acetate/hexane solution gives the title product as an oil (12.5 g, 92.6% yield).

Workup

  1. temperaturerefluxed for 2.5 hours
  2. temperaturecooled to room temperature
  3. filtrationThe resultant mixture is filtered through diatomaceous earth
  4. concentrationconcentrated in vacuo
  5. customto obtain a residue

Sources & evidence

ORD record
ord-9fa17158c64842998c5424c7d3a9dbd7
Source dataset
uspto-grants-2001_05
Patent number
US06235754B1

Reaction notes

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