Tributylvinyltin → HCID 69587393, compound

HRID 2211573Notes

Reaction equation

HRID 2211573 reaction equation
[C:1]1([CH3:21])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[C:9]([NH:13][C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[CH:10]=[CH:11][CH:12]=1.[CH2:22]([Sn](CCCC)(CCCC)C=C)[CH2:23]CC>C(C1C(O)=CC=C(CCCC)C=1C)CCC.C1(C)C=CC=CC=1>[C:1]1([CH3:21])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[C:9]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH:22]=[CH2:23])=[CH:16][CH:15]=2)[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 69588032HCID 69588032, compound

Product 1

HCID 69587393HCID 69587393, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 20510296HCID 20510296, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

In a reactor equipped with a stirrer and a reflux condenser, 2.0 g (0.0059 mol) of m-tolyl(p-bromophenyl)phenylamine, 0.18 g (0.00015 mol) of tetrakistriphenylphosphine palladium (0), 0.005 g of 2,6-dibutylhydroxytoluene and 20 ml of toluene were added and dissolved, and then 2.1 ml (0.0071 mol) of tributyl(vinyl)tin was added to the mixture in an argon gas atmosphere at room temperature. The mixture was heated to 100° C. and continuously stirred for 76 hours. After air cooling, the solvent was distilled off, and the residue was purified by silica gel column chromatography (developing solvent: hexane) to yield 1.4 g of m-tolyl(p-vinylphenyl)phenylamine as a colorless liquid at a yield of 81%.

Workup

  1. customIn a reactor equipped with a stirrer and a reflux condenser
  2. dissolutiondissolved
  3. temperatureAfter air cooling
  4. distillationthe solvent was distilled off
  5. customthe residue was purified by silica gel column chromatography (developing solvent: hexane)

Sources & evidence

ORD record
ord-446c226ae74d4be7be62ade4a971e583
Source dataset
uspto-grants-2006_09
Patent number
US07101630B2

Reaction notes

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