Potassium Carbonate → 4,5-Dihydro-6-oxa-1-thia-benzo[e]azulene-9-carbonitrile

HRID 84427Notes

Reaction equation

HRID 84427 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][C:13]1[CH:17]=[CH:16][S:15][CH:14]=1)[C:5]#[N:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[S:15]1[C:14]2[C:2]3[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[CH:8][C:9]=3[O:10][CH2:11][CH2:12][C:13]=2[CH:17]=[CH:16]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 568341533-Bromo-4-(2-thiophen-3-yl-ethoxy)-benzonitrile

Product 1

HCID 568341544,5-Dihydro-6-oxa-1-thia-benzo[e]azulene-9-carbonitrile

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3-bromo-4-(2-thiophen-3-yl-ethoxy)-benzonitrile (4.50 g) in DMF (20 mL) was added palladium acetate (327 mg), triphenylphosphine (766 mg) and potassium carbonate (4.03 g) and the reaction heated at 90° C. for 16 h. After cooling to room temperature the mixture was diluted with ethyl acetate (60 ml) and filtered. The filtrate was washed with brine (80 mL), dried (MgSO4), reduced in vacuo and purified on silica to give 4,5-dihydro-6-oxa-1-thia-benzo[e]azulene-9-carbonitrile.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. filtrationfiltered
  3. washThe filtrate was washed with brine (80 mL)
  4. dry with materialdried (MgSO4)
  5. custompurified on silica

Sources & evidence

ORD record
ord-1d9fc3f3b58d4769945d1f1ac71388b1
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Reaction notes

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