Hydrochloric Acid → HCID 66751041, compound

HRID 2390967Notes

Reaction equation

HRID 2390967 reaction equation
Br[C:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[C:17]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])#[N:18].Cl>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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C.O.COCCOC>[S:10]1[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH:19]([C:17]#[N:18])[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:7]=2[CH:8]=[CH:9]1

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 70693tert-Butyl cyanoacetateHCID 120942084-Bromobenzo[b]thiopheneHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 66751041HCID 66751041, compoundYield 67.6%

Reagents, catalysts & solvents 5

HCID 11776TriphenylphosphineCatalyst2×HCID 178418476HCID 178418476, compoundCatalyst2×HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1,2-dimethoxyethane (3 mL) solution of 0.30 g of 4-bromobenzothiophene were added 0.33 g of potassium tert-butoxide, 0.21 g of tert-butyl cyanoacetate, 0.01 g of dichlorobis(triphenylphosphine)palladium(II) and 0.01 g of triphenylphosphine, which was then refluxed for 40 minutes. Thereto were added 0.33 g of potassium tert-butoxide, 0.01 g of dichlorobis(triphenylphosphine)palladium(II) and 0.01 g of triphenylphosphine, which was then refluxed for 30 minutes. The reaction mixture was added to a mixed solution of water and ethyl acetate, and the pH was adjusted to 1 with 6 mol/L hydrochloric acid. The organic layer was separated, and dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The resultant residue was purified using silica gel column chromatography (eluent; hexane:ethyl acetate=5:1) to provide 0.26 g of tert-butyl 2-(1-benzothiophen-4-yl)-2-cyanoacetate as pale brown oily form.

Workup

  1. temperaturewas then refluxed for 40 minutes
  2. temperaturewas then refluxed for 30 minutes
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationby distilling off the solvent under reduced pressure
  6. customThe resultant residue was purified

Sources & evidence

ORD record
ord-8981a7372d6a40ef8ff2b40e0316e23f
Source dataset
uspto-grants-2012_09
Patent number
US08273902B2

Reaction notes

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