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

HRID 240288노트

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HRID 240288 반응식
Br[CH2:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[Cl:10].[Na+].[I-].[C:13]([S-:15])#[N:14].[K+]>CN(C=O)C.O>[Cl:10][C:4]1[CH:5]=[CH:6][C:7]([F:9])=[CH:8][C:3]=1[CH2:2][N:14]=[C:13]=[S:15]

참가 물질

6

반응물 3

HCID 5238Sodium IodideHCID 516872Potassium thiocyanateHCID 27736232-Chloro-5-fluorobenzyl bromide

생성물 1

HCID 866548531-Chloro-4-fluoro-2-(isothiocyanatomethyl)benzene

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

To a solution of 2-(bromomethyl)-1-chloro-4-fluorobenzene (25, 22.3 g, 100 mmol) in dry DMF (150 mL) were added NaI (16.0 g, 107 mmol) and KSCN (19.5 g, 200 mmol) The mixture was heated under N2 at 90° C. for 18 h. After cooling to RT, the mixture was diluted with water (200 mL), and extracted with EtOAc (200 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-chloro-4-fluoro-2-(isothiocyanatomethyl)benzene (26).

후처리

  1. temperatureAfter cooling to RT
  2. extractionextracted with EtOAc (200 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-9f11df4a5af54f37bed26d2d29688d72
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648073B2

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