Triphenylphosphine → 5-Ethenyl-1,3-dihydro-2H-2-benzothiophene-2,2-dione

HRID 453604

Reaction equation

HRID 453604 reaction equation
Br[C:2]1[CH:12]=[CH:11][C:5]2[CH2:6][S:7](=[O:10])(=[O:9])[CH2:8][C:4]=2[CH:3]=1.[CH:13]1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=C[CH:14]=1.C([Si](C)(C)C)=C>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:13]([C:2]1[CH:12]=[CH:11][C:5]2[CH2:6][S:7](=[O:10])(=[O:9])[CH2:8][C:4]=2[CH:3]=1)=[CH2:14]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 79102VinyltrimethylsilaneHCID 2883965-Bromo-1,3-dihydro-benzo(c)thiophene 2,2-dioxide

Product 1

HCID 598014795-Ethenyl-1,3-dihydro-2H-2-benzothiophene-2,2-dione

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

Under classical Heck reaction conditions, 5-Bromo-1,3-dihydro-benzo[c]thiophene 2,2-dioxide was transformed with PPh3, Pd(OAc)2, TEA, and vinyltrimethylsilane at 90° C. in DMF. The crude product was extracted with CH2Cl2 and concentrated. Deprotection in CH2Cl2/TFA gave the pure product after purification with flash chromatography (CH2Cl2) in high yields.

Workup

  1. extractionThe crude product was extracted with CH2Cl2
  2. concentrationconcentrated
  3. customDeprotection in CH2Cl2/TFA gave the pure product
  4. customafter purification with flash chromatography (CH2Cl2) in high yields

Sources & evidence

ORD record
ord-5eaaf0e269454a8a85cd962bc79c425b
Source dataset
uspto-grants-2013_07
Patent number
US08492510B2

Linked notes

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