Perfluorohexane → trans-Stilbene

HRID 2182834

Reaction equation

HRID 2182834 reaction equation
[C:1](F)(F)([C:12](F)(F)[C:13](F)(F)F)[C:2](F)(F)[C:3](F)(F)[C:4](F)(F)F.[Br:21]/[CH:22]=[CH:23]/[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1([Zn]I)C=CC=CC=1>CC#N.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]1(/[CH:22]=[CH:23]/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:12]=[CH:13][CH:4]=[CH:3][CH:2]=1.[Br:21]/[CH:22]=[CH:23]/[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 3

HCID 9639PerfluorohexaneHCID 5314126trans-beta-BromostyreneHCID 178506618HCID 178506618, compound

Product 2

HCID 638088trans-StilbeneHCID 5314126trans-beta-Bromostyrene

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

FC-72 (10 mL) was charged to the U-tube (F-phase), a solution of (E)-bromostyrene (130 μL, 1.0 mmol) in MeCN (1 mL) was charged to the S-phase of the U-tube and a solution of Pd(PPh3)4 (23 mg, 0.02 mmol) in toluene (1.5 mL) was charged to the P-phase of the U-tube. After PhZnI (0.5 M in THF, 1.0 mL) was added to the P-phase, each phase was stirred for 1 day. The mixture in the P-phase was decanted into water, extracted with ether, dried over MgSO4 and then evaporated. However, trans-stilbene was not obtained in the P-phase and (E)-bromostyrene was recovered from the S-phase.

Workup

  1. customThe mixture in the P-phase was decanted into water
  2. extractionextracted with ether
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-e713d16a3d6d4f14baf34125392028ca
Source dataset
uspto-grants-2005_05
Patent number
US06897331B2

Linked notes

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