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

HRID 1472769ノート

反応式

HRID 1472769 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8bdaa99b9d2843429bd42ddfd2ead309
出典データセット
uspto-grants-2015_04
特許番号
US09012655B2

反応ノート

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