Sodium Iodide → 1-Bromo-4-fluoro-2-(isothiocyanatomethyl)benzene

HRID 240276

반응식

HRID 240276 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9]Br.[Na+].[I-].[C:13]([S-:15])#[N:14].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][N:14]=[C:13]=[S:15]

참가 물질

6

반응물 3

HCID 5238Sodium IodideHCID 516872Potassium thiocyanateHCID 5179721-Bromo-2-(bromomethyl)-4-fluorobenzene

생성물 1

HCID 866548501-Bromo-4-fluoro-2-(isothiocyanatomethyl)benzene

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a solution of 1-bromo-2-(bromomethyl)-4-fluorobenzene (12, 5.36 g, 20.0 mmol) in dry DMF (20 mL) was added NaI (1.20 g, 8.00 mmol) and KSCN (3.88 g, 40.0 mmol). The mixture was heated under N2 at 80° C. for 12 h. After cooling to RT, the mixture was diluted with water (100 mL), and extracted with EtOAc (50 mL×2). The combined extracts were washed with brine, dried over MgSO4 and concentrated to give crude product. This was purified by column chromatography on silica gel, and eluted with petroleum ether to provide 1-bromo-4-fluoro-2-(isothiocyanatomethyl)benzene (13).

후처리

  1. temperatureAfter cooling to RT
  2. extractionextracted with EtOAc (50 mL×2)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give crude product
  7. customThis was purified by column chromatography on silica gel
  8. washeluted with petroleum ether

출처 및 근거

ORD 기록
ord-5dcaa496b0594bcb9620f803335dbacb
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648073B2

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