Ammonia → 3-Bromo-5-ethylbenzonitrile

HRID 539299ノート

反応式

HRID 539299 の反応式
Br[C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[CH:5]=[C:4]([Br:10])[CH:3]=1.[Cu](C#N)[C:12]#[N:13].N1C=CC=CC=1.N>CN(C=O)C.O>[Br:10][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([CH2:8][CH3:9])[CH:5]=1)[C:12]#[N:13]

参加物

7

反応物 4

HCID 222AmmoniaHCID 1049PyridineHCID 187118073,5-DibromoethylbenzeneHCID 178418260HCID 178418260、化合物

生成物 1

HCID 679795883-Bromo-5-ethylbenzonitrile

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

A mixture of 1,3-dibromo-5-ethylbenzene (2.7 g, 10.2 mmol), copper cyanide (0.916 g, 10.2 mmol), pyridine (1.65 mL, 20.5 mmol) in DMF (15 mL) was heated at 150° C. for 3 h. After cooling to r.t., the mixture was poured into a solution of H2O (30 mL) and ammonia (25% aq. Solution, 20 mL) and extracted with EtOAc. The combined organic layer was dried (MgSO4), filtered and concentrated in vacuo. The product was purified using flash chromatography on silica gel, gradient elution of 0-60% EtOAc in n-heptane. GCMS (CI) m/z 210 [M+1]+.

後処理

  1. temperatureAfter cooling to r.t.
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe product was purified
  7. washon silica gel, gradient elution of 0-60% EtOAc in n-heptane

出典と根拠

ORDレコード
ord-b95a28911d2b45b0addc82afb37b60d6
出典データセット
uspto-grants-2014_10
特許番号
US08865911B2

反応ノート

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