Sodium Chloride → 4-[(5-Nitro-thien-2-yl)ethynyl]benzonitrile

HRID 1627

반응식

HRID 1627 반응식
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)#[CH:2].Br[C:12]1[S:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=1.C(N(CC)CC)C.[Cl-].[Na+]>CN(C)C=O.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(OCC)(=O)C>[N+:17]([C:14]1[S:13][C:12]([C:2]#[C:1][C:3]2[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=2)=[CH:16][CH:15]=1)([O-:19])=[O:18]

참가 물질

8

반응물 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 832222-Bromo-5-nitrothiopheneHCID 45472454-Ethynylbenzonitrile

생성물 1

HCID 196919534-[(5-Nitro-thien-2-yl)ethynyl]benzonitrile

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-ethynylbenzonitrile (0.5 g), 2-bromo-5-nitrothiophene (0.9 g) and bis(triphenylphosphine)palladium dichloride (83 mg) in anhydrous dimethylformamide (4 ml) was added triethylamine (2.2 ml). The reaction mixture was stirred at room temperature for 3 days then ethyl acetate (200 ml) and saturated sodium chloride (200 ml) were added. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The crude solid was triturated with 1:1 dichloromethane/hexane followed by diethyl ether to give 4-[(5-nitro-2-thienyl)ethynyl]benzonitrile as a yellow solid.

후처리

  1. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  2. filtrationfiltered
  3. customevaporated to dryness
  4. customThe crude solid was triturated with 1:1 dichloromethane/hexane

출처 및 근거

ORD 기록
ord-f537d62089cd4cba9bc833054c2f705b
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726195

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