Water → HCID 85774200, compound

HRID 1726827Notes

Reaction equation

HRID 1726827 reaction equation
O.[C:2]1([P:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:21][CH2:22][I:23]>C1C=CC=CC=1>[I-:23].[F:21][CH2:22][P+:8]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 13981373Fluoro(iodo)methane

Product 1

HCID 85774200HCID 85774200, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

An alternate synthesis of the vinylic fluorinated variant of 3,4-cyclopropyl-heptadecanoic acid can be achieved from the ketone compound described above (FIG. 12). A modified version of the mechanism is from Burton and Greenlimb 1975. J. Org. Chem. 40: 2796-2801; and in Schlosser and Zimmermann 1969. Synthesis 1: 75-76. Fluoromethyltriphenylphosphonium iodide was synthesized in a round-bottomed flask fitted with a water-cooled reflux condenser. The flask was charged with triphenylphosphine and fluoroiodomethane in dry benzene. The resulting solution was refluxed for 64 hr with moderate stirring. Upon completion of the reaction, the white insoluble phosphonium salt was collected on a glass funnel, washed with hot benzene, and dried in a vacuum dessicator for 12 hr.

Workup

  1. customSynthesis 1: 75-76
  2. temperaturecooled
  3. temperaturereflux condenser
  4. temperatureThe resulting solution was refluxed for 64 hr with moderate stirring
  5. customUpon completion of the reaction
  6. customthe white insoluble phosphonium salt was collected on a glass funnel
  7. washwashed with hot benzene
  8. customdried in a vacuum dessicator for 12 hr

Sources & evidence

ORD record
ord-dca71dd8bf154fc59a6b9de576cf4e7f
Source dataset
uspto-grants-2009_02
Patent number
US07494642B2

Reaction notes

Loading…