Bromobenzene → HCID 19981420, compound

HRID 1460990Notes

Reaction equation

HRID 1460990 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[S:7][C:8]([C:11]#[C:12][C:13]2[S:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[CH:17]=2)=[CH:9][CH:10]=1)CCC.Br[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:31]1([C:6]2[S:7][C:8]([C:11]#[C:12][C:13]3[S:14][C:15]4[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=4[CH:17]=3)=[CH:9][CH:10]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 2

HCID 7961BromobenzeneHCID 19981412HCID 19981412, compound

Product 1

HCID 19981420HCID 19981420, compoundYield 46.6%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1.0 gram (0.0019 mole) of tributyl 5-(benzothien-2-ylethynyl)thien-2-yltin and 0.33 gram (0.0021 mole) of bromobenzene in 10 ml of tetrahydrofuran was added a catalytic amount of bis(triphenylphosphine)palladium(II) chloride. Upon completion of addition, the reaction mixture was warmed to reflux where it was stirred for 18 hours. After this time the reaction mixture was cooled to ambient temperature, and then it was subjected to column chromatography on silica gel. Elution was accomplished with hexane. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.28 gram of 2-(5-phenylthien-2-ylethynyl)benzothiophene; m.p. 185°-186.5° C. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. temperaturethe reaction mixture was warmed
  3. temperatureto reflux where it
  4. washElution
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9c9da073e4774351a938160fafd0c926
Source dataset
uspto-grants-1991_12
Patent number
US05073564

Reaction notes

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