Bromobenzene → p-Vinylbiphenyl

HRID 13891

Reaction equation

HRID 13891 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:8]([C:10]1[CH:15]=[CH:14][C:13]([Mg]Cl)=[CH:12][CH:11]=1)=[CH2:9].[Cl-].[NH4+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC([B-](C2C=CC(C)=CC=2)(C2C=CC(C)=CC=2)C2C=CC(C)=CC=2)=CC=1.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.O1CCCC1>[CH:8]([C:10]1[CH:15]=[CH:14][C:13]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:12][CH:11]=1)=[CH2:9]

Participants

7

Reactant 3

HCID 7961BromobenzeneHCID 25517Ammonium ChlorideHCID 178436504HCID 178436504, compound

Product 1

HCID 16883p-Vinylbiphenyl

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 23136639Tri-tert-butylphosphonium tetra-para-tolylborateCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A 100-ml four-necked flask was equipped with a stirrer, a thermometer, a dropping funnel and a reflux condenser. 0.0674 g (0.3 mmol) of palladium (II) acetate and 6 ml of tetrahydrofuran were weighed in the flask, followed by stirring. Further, 0.347 g (0.6 mmol) of tri-tert-butylphosphonium tetra-para-tolylborate obtained in Example B-3 was weighed in air and added into the flask. The flask was purged with argon, followed by stirring at 19° C. for 30 minutes. 4.710 g (30 mmol) of bromobenzene was added, followed by stirring at 19° C. for 30 minutes. 40 ml (50 mmol) of 1.25M tetrahydrofuran solution of 4-vinylphenylmagnesium chloride was added dropwise at 19° C. over a period of 2 hours, followed by stirring at 30° C. for 2 hours. After the completion of the reaction, 10 ml of saturated aqueous ammonium chloride solution was added, followed by separation. The organic phase was purified by column chromatography to afford 4.434 g of 4-vinylbiphenyl (yield: 82 mol % based on bromobenzene). The identification of the product was made by mass spectroscopy.

Workup

  1. customA 100-ml four-necked flask was equipped with a stirrer
  2. additionadded into the flask
  3. customThe flask was purged with argon
  4. stirringby stirring at 19° C. for 30 minutes
  5. stirringby stirring at 19° C. for 30 minutes
  6. stirringby stirring at 30° C. for 2 hours
  7. additionwas added
  8. customfollowed by separation
  9. customThe organic phase was purified by column chromatography

Sources & evidence

ORD record
ord-f0d18183e23e46fc8d9fc0c713951e53
Source dataset
uspto-grants-2010_06
Patent number
US07728176B2

Linked notes

Loading…