Sodium Carbonate → 4,5-Bis(4-chloro-2-methylphenyl)thiophene-2-carbonitrile

HRID 1472769노트

반응식

HRID 1472769 반응식
Br[C:2]1[CH:3]=[C:4]([C:8]#[N:9])[S:5][C:6]=1Br.[Cl:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[C:13]([CH3:20])[CH:12]=1.O1[CH2:26][CH2:25]OCC1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:3]=[C:4]([C:8]#[N:9])[S:5][C:6]=2[C:14]2[CH:13]=[CH:12][C:11]([Cl:10])=[CH:16][C:25]=2[CH3:26])=[C:13]([CH3:20])[CH:12]=1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 5017600(4-Chloro-2-methylphenyl)boronic acidHCID 232622764,5-Dibromothiophene-2-carbonitrile

생성물 1

HCID 682936344,5-Bis(4-chloro-2-methylphenyl)thiophene-2-carbonitrile수율 84%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

A round-bottomed flask was charged with 4,5-dibromothiophene-2-carbonitrile (534 mg, 2.00 mmol), 4-chloro-2-methylphenylboronic acid (818 mg, 4.80 mmol) and Pd(PPh3)4 (136 mg, 0.10 mmol). After degassed, dioxane (10 mL) and aqueous sodium carbonate (5 mL, 2M, 10 mmol) was added. The reaction mixture was heated to 90° C. The progress of the reaction was monitored by TLC. After the reaction was complete, 50 mL of water was added, and the reaction mixture was extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulphate and then concentrated. The residue was purified by flash chromatography (hexane:CH2Cl2=2:1). 0.60 g (84%) of product was obtained as clear oil.

후처리

  1. customAfter degassed
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (hexane:CH2Cl2=2:1)

출처 및 근거

ORD 기록
ord-8bdaa99b9d2843429bd42ddfd2ead309
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012655B2

반응 노트

불러오는 중…