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

HRID 627855Notes

Reaction equation

HRID 627855 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-ecba0b9712a3434790bb158489825dff
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Reaction notes

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