Triphenylphosphine → HCID 178455762, compound

HRID 1600467Notes

Reaction equation

HRID 1600467 reaction equation
[Br:1][C:2](Br)(Br)[F:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:25]([C@H:27]1[CH2:32][CH2:31][C@H:30]([C@H:33]2[CH2:38][CH2:37][C@H:36]([CH:39]=O)[CH2:35][CH2:34]2)[CH2:29][CH2:28]1)[CH3:26]>COCCOC.O1CCCC1>[CH2:25]([C@H:27]1[CH2:32][CH2:31][C@H:30]([C@H:33]2[CH2:38][CH2:37][C@H:36]([CH:39]=[C:2]([F:3])[Br:1])[CH2:35][CH2:34]2)[CH2:29][CH2:28]1)[CH3:26]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 67707TribromofluoromethaneHCID 178455770HCID 178455770, compound

Product 1

HCID 178455762HCID 178455762, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of tribromofluoromethane and triphenyl phosphine in ethylene glycol dimethyl ether was stirred at 70° C. for 1 hour. The reaction solution was cooled with ice, and a solution of trans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde in tetrahydrofuran was added thereto. After the reaction solution was further stirred for 1 hour, the temperature of the solution was gradually raised up to room temperature, and insoluble substances were removed by filtration. Dilute hydrochloric acid was added to the filtrate, and it was extracted with toluene. After the organic layer was washed with water, it was dried by using anhydrous magnesium sulfate, and concentrated under a reduced pressure to obtain a brown oily product. After this product was purified by using a silica gel column chromatography, it was recrystallized from heptane to obtain trans-4-(trans-4-ethylcyclohexyl)cyclohexyl-2-fluoro-2-bromoethene.

Workup

  1. temperatureThe reaction solution was cooled with ice
  2. customwere removed by filtration
  3. additionDilute hydrochloric acid was added to the filtrate, and it
  4. extractionwas extracted with toluene
  5. washAfter the organic layer was washed with water, it
  6. customwas dried
  7. concentrationconcentrated under a reduced pressure
  8. customto obtain a brown oily product
  9. customAfter this product was purified
  10. customwas recrystallized from heptane

Sources & evidence

ORD record
ord-0ef7506cc8324ddcb4daf9be46433a35
Source dataset
uspto-grants-1999_11
Patent number
US05976408

Reaction notes

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