Sodium Cyanide → 2-(4-Bromo-2-fluorophenyl)acetonitrile

HRID 7698

반응식

HRID 7698 반응식
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[C:4]([F:10])[CH:3]=1.[C-:11]#[N:12].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][C:11]#[N:12])=[C:4]([F:10])[CH:3]=1

참가 물질

4

반응물 2

HCID 8929Sodium CyanideHCID 27336604-Bromo-2-fluorobenzyl bromide

생성물 1

HCID 71723082-(4-Bromo-2-fluorophenyl)acetonitrile

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

To a stirred solution of 4-bromo-2-fluoro benzyl bromide (1.5 g, 5.6 mmol) in DMF (50 mL) was added sodium cyanide (0.8 g, 17 mmol). The reaction mixture was stirred at 90° C. for 1 h, cooled to rt and quenched with brine (50 mL). After extraction with EtOAc (3×100 mL), the organic layers were combined, washed with brine (50 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, hexanes:EtOAc 5:1) to afford 4-bromo-2-fluoro benzyl cyanide as yellow solid. MS (ESI) 307 (M+H)+.

후처리

  1. temperaturecooled to rt
  2. customquenched with brine (50 mL)
  3. extractionAfter extraction with EtOAc (3×100 mL)
  4. washwashed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (silica gel, hexanes:EtOAc 5:1)

출처 및 근거

ORD 기록
ord-bdc28b5ce6e24691832732f0a37423ba
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087601B2

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