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

HRID 930926

Reaction equation

HRID 930926 reaction equation
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

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 24437Sodium SulfiteHCID 516892Sodium Bicarbonate2×HCID 27936265-Bromo-6-chloropyridine-3-sulfonyl chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-84952ea5e3604f048e593a31dd7ee4df
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Linked notes

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