N,N-二甲基甲酰胺 → 3-乙基苯腈

HRID 732002笔记

反应方程式

HRID 732002 反应方程式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH3:9])[CH:3]=1.[CH3:10][N:11](C=O)C>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.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>[C:10]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH3:9])[CH:3]=1)#[N:11]

参与物

6

反应物 2

HCID 6228N,N-二甲基甲酰胺HCID 1231701-溴-3-乙基苯

产物 1

HCID 966923-乙基苯腈

试剂、催化剂与溶剂 3

HCID 11186氰化锌催化剂HCID 178418397HCID 178418397，化合物催化剂HCID 8857乙酸乙酯溶剂

反应条件

温度
80 °C

实验过程

Argon was bubbled into a solution of 1-bromo-3-ethylbenzene (2.5 g, 13.5 mmol) in DMF (37 ml) for 10 min. and then zinc cyanide (1.75 g, 14.9 mmol) and tetrakis(triphenylphosphine)palladium(0) (1.56 g, 1.35 mmol) were added. After stirring at 80° C. overnight the reaction mixture was diluted with ethyl acetate (35 ml) then filtered through celite to remove the precipitate. The filtrate was washed with water (3×), saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. The product was purified by flash column chromatography using 2% ethyl acetate in hexane affording a colorless liquid (1.42 g). GC-MS (M+): 131.18.

后处理

  1. filtrationthen filtered through celite
  2. customto remove the precipitate
  3. washThe filtrate was washed with water (3×), saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was purified by flash column chromatography

来源与证据

ORD记录
ord-0a24c6d7c22f4dd6a1791c01d3a2e967
来源数据集
uspto-grants-2009_09
专利号
US07585881B2

反应笔记

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