Triphenylphosphine → HCID 86744367, compound

HRID 1110405Notes

Reaction equation

HRID 1110405 reaction equation
[Cl:1][CH2:2][CH:3]=[C:4]([CH:16]1[CH2:18][CH2:17]1)[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:15])([F:14])[F:13])=[CH:7][CH:6]=1.[C:19]1([P:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[Cl-:1].[CH:16]1([C:4]([C:5]2[CH:10]=[CH:9][C:8]([O:11][C:12]([F:15])([F:14])[F:13])=[CH:7][CH:6]=2)=[CH:3][CH2:2][P+:25]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 537327453-Chloro-1-cyclopropyl-1-(4-trifluoromethoxyphenyl)-1-propene

Product 1

HCID 86744367HCID 86744367, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 113.5 grams (0.41 mole) of 3-chloro-1-cyclopropyl-1-(4-trifluoromethoxyphenyl)-1-propene and 113.0 grams (0.43 mole) of triphenylphosphine in 400 mL of toluene was heated at reflux for 4 hours. After this time the reaction mixture was cooled and concentrated under reduced pressure to a residue. The residue was triturated with 1000 mL of diethyl ether. The ether was decanted from the residue, and the residue was triturated with two more 1000 mL portions of diethyl ether in the manner described above. The solid residue was dried under reduced pressure yielding 176.0 grams of [3-cyclopropyl-3-(4-trifluoromethoxyphenyl)-2-propen-1-yl]triphenylphosphonium chloride.

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureAfter this time the reaction mixture was cooled
  3. concentrationconcentrated under reduced pressure to a residue
  4. customThe residue was triturated with 1000 mL of diethyl ether
  5. customThe ether was decanted from the residue
  6. customthe residue was triturated with two more 1000 mL portions of diethyl ether in the manner
  7. customThe solid residue was dried under reduced pressure

Sources & evidence

ORD record
ord-beb3490793244da9858492292b692270
Source dataset
uspto-grants-1990_12
Patent number
US04975451

Reaction notes

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