Sodium Iodide → 2-Iodo-4-[3-(trifluoromethoxy)phenyl]pyridine

HRID 2207643노트

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HRID 2207643 반응식
C(Cl)(=O)C.Cl[C:6]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=2)[CH:9]=[CH:8][N:7]=1.[I-:23].[Na+].C(=O)([O-])[O-].[Na+].[Na+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>CC#N.CCOC(C)=O.O>[I:23][C:6]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=2)[CH:9]=[CH:8][N:7]=1

참가 물질

9

반응물 5

HCID 5238Sodium Iodide2회HCID 6367Acetyl chlorideHCID 10340Sodium CarbonateHCID 656671Sodium PyrosulfiteHCID 896497812-Chloro-4-(3-(trifluoromethoxy)phenyl)pyridine

생성물 1

HCID 896493782-Iodo-4-[3-(trifluoromethoxy)phenyl]pyridine수율 107%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

Acetyl chloride (4.45 mL, 62.6 mmol) was added to a solution of 2-chloro-4-[3-(trifluoromethoxy)phenyl]-pyridine [CAS 1261856-64-7](11.42 g, 41.73 mmol) and sodium iodide (31.28 g, 208.67 mmol) in MeCN (200 mL) under N2, and the resulting suspension was heated at 80° C. for 18 hrs. Additional sodium iodide was added (20 mol %) and stirring was continued for 3 hrs. The reaction was cooled and the mixture was treated with aqueous sodium carbonate. After 5 minutes, solid sodium metabisulphite was added until decolourisation achieved. Water was added to redissolve a precipitate which had formed. The mixture was diluted with EtOAc and the layers separated. The aqueous layer was washed with EtOAc (2x), the combined organics were dried (MgSO4) and the solvent evaporated to afford the crude 2-iodo-4-[3-(trifluoromethoxy)phenyl]pyridine (D105) (16.3 g) as a amber oil containing about ˜5% of reduced 2-H material and ˜8% of unreacted chloride starting material;

후처리

  1. temperatureThe reaction was cooled
  2. waitAfter 5 minutes
  3. dissolutionto redissolve a precipitate which
  4. customhad formed
  5. customthe layers separated
  6. washThe aqueous layer was washed with EtOAc (2x)
  7. dry with materialthe combined organics were dried (MgSO4)
  8. customthe solvent evaporated

출처 및 근거

ORD 기록
ord-f2f47785b669408f9e61181f65129054
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376436B2

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