Ammonia → 3-Bromo-5-ethylbenzonitrile

HRID 539299노트

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HRID 539299 반응식
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]

참가 물질

7

반응물 4

HCID 222AmmoniaHCID 1049PyridineHCID 187118073,5-DibromoethylbenzeneHCID 178418260HCID 178418260, 화합물

생성물 1

HCID 679795883-Bromo-5-ethylbenzonitrile

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
150 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-b95a28911d2b45b0addc82afb37b60d6
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865911B2

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