Triphenylphosphine → HCID 22219251, compound

HRID 2072709Notes

Reaction equation

HRID 2072709 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5](C[Br:7])=[CH:4][CH:3]=1.[C:10]1([P:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(#N)C>[Br-:7].[F:1][C:2]1[CH:3]=[CH:4][C:5]([P+:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 680214-Fluorobenzyl bromide

Product 1

HCID 22219251HCID 22219251, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

98.6 g (0.52 mol) of 4-fluorobenzyl bromide (XIV, R1 =4-fluorophenyl, X=Br) and 136.7 g (0.52 mol) of triphenylphosphine in 400 ml of acetonitrile are boiled under reflux for 6 hours. After cooling, the mixture is concentrated to one half the volume in vacuo, cooled in an ice bath, and the crystals which have separated out are filtered off with suction and washed with cold acetonitrile and diethyl ether. The crystals are thoroughly dried in vacuo at 100° C.

Workup

  1. temperatureunder reflux for 6 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated to one half the volume in vacuo
  4. temperaturecooled in an ice bath
  5. customthe crystals which have separated out
  6. filtrationare filtered off with suction
  7. washwashed with cold acetonitrile and diethyl ether
  8. customThe crystals are thoroughly dried in vacuo at 100° C.

Sources & evidence

ORD record
ord-70589360b3104f1caa1643d8a7b229af
Source dataset
uspto-grants-1990_04
Patent number
US04914127

Reaction notes

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