Potassium Fluoride → 4-Bromo-5-(4-methylnaphthalen-1-yl)thiophene-2-carbonitrile

HRID 1472771ノート

反応式

HRID 1472771 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:8]#[N:9])[S:5][C:6]=1Br.[CH3:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](B(O)O)=[CH:13][CH:12]=1.[F-].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:1][C:2]1[CH:3]=[C:4]([C:8]#[N:9])[S:5][C:6]=1[C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:11]([CH3:10])=[CH:12][CH:13]=1

参加物

5

反応物 3

HCID 522689Potassium FluorideHCID 27735114-Methyl-1-naphthaleneboronic acidHCID 232622764,5-Dibromothiophene-2-carbonitrile

生成物 1

HCID 682936224-Bromo-5-(4-methylnaphthalen-1-yl)thiophene-2-carbonitrile収率 88.4%

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

実験手順

A round-bottomed flask was charged with 4,5-dibromothiophene-2-carbonitrile (536 mg, 2.00 mmol), 4-methylnaphthalen-1-ylboronic acid (409 mg, 2.20 mmol), Pd2(dba)3 (18.3 mg, 0.020 mmol) and KF (383 mg, 6.60). After degassed, dioxane (5 mL) and P(Bu-t)3 (0.24 mL, 0.2M, 0.048 mmol) was added. The reaction mixture was stirred at rt until complete. 30 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=3:1). 0.58 g (88%) of product was obtained as a white solid.

後処理

  1. customAfter degassed
  2. additiondioxane (5 mL) and P(Bu-t)3 (0.24 mL, 0.2M, 0.048 mmol) was added
  3. addition30 mL of water was added
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (hexane:CH2Cl2=3:1)

出典と根拠

ORDレコード
ord-99eaff835a184249a65a657b5e3a0282
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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