Iodoethane → 3-Bromo-2-chloro-5-(ethylsulfonyl)pyridine

HRID 930926

반응식

HRID 930926 반응식
S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+].[Br:12][C:13]1[C:14]([Cl:23])=[N:15][CH:16]=[C:17]([S:19](Cl)(=[O:21])=[O:20])[CH:18]=1.I[CH2:25][CH3:26]>O>[Br:12][C:13]1[C:14]([Cl:23])=[N:15][CH:16]=[C:17]([S:19]([CH2:25][CH3:26])(=[O:21])=[O:20])[CH:18]=1

참가 물질

6

반응물 4

HCID 6340IodoethaneHCID 24437Sodium SulfiteHCID 516892Sodium Bicarbonate2회HCID 27936265-Bromo-6-chloropyridine-3-sulfonyl chloride

생성물 1

HCID 593265653-Bromo-2-chloro-5-(ethylsulfonyl)pyridine

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
75 °C

실험 절차

Sodium sulfite (1.755 g, 13.92 mmol) and sodium bicarbonate (1.231 g, 14.65 mmol) were dissolved in water (37 mL) to give a colorless solution. The mixture was heated at 75° C. 3-Bromo-2-chloropyridine-5-sulfonyl chloride (2.132 g, 7.33 mmol) was added portionwise over 1 hour. The reaction mixture was stirred at 75° C. for 1 hour. The mixture was concentrated and N,N-dimethylformamide (13.88 mL) was added. Sodium bicarbonate (1.231 g, 14.65 mmol) and iodoethane (0.589 mL, 7.33 mmol) were added. The resulting mixture was heated to 75° C. for 2 hours and then cooled to ambient temperature. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (silica gel, 0-100% ethyl acetate/heptane) to provide the title compound.

후처리

  1. customto give a colorless solution
  2. concentrationThe mixture was concentrated
  3. additionN,N-dimethylformamide (13.88 mL) was added
  4. temperatureThe resulting mixture was heated to 75° C. for 2 hours
  5. temperaturecooled to ambient temperature
  6. customThe mixture was partitioned between ethyl acetate and water
  7. washThe organic layer was washed with saturated aqueous sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by flash chromatography (silica gel, 0-100% ethyl acetate/heptane)

출처 및 근거

ORD 기록
ord-84952ea5e3604f048e593a31dd7ee4df
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296741B2

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