Sodium methanesulfinate → HCID 58255826, compound

HRID 241049Notes

Reaction equation

HRID 241049 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9]Cl)[C:5]([Cl:8])=[N:6][CH:7]=1.[CH3:11][S:12]([O-:14])=[O:13].[Na+]>O1CCOCC1.O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][S:12]([CH3:11])(=[O:14])=[O:13])[C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 2733271Sodium methanesulfinateHCID 425443105-Bromo-2-chloro-3-(chloromethyl)pyridine

Product 1

HCID 58255826HCID 58255826, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-bromo-2-chloro-3-(chloromethyl)pyridine (124 mg, 0.52 mmol) and sodium methanesulfinate (52 mg, 0.52 mmol) in dioxane (1.4 mL) and water (1.4 mL) was heated to 110° C. in a microwave reactor for 15 min. After cooling to rt, water was added to the reaction mixture which was subsequently extracted twice with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo to provide 5-bromo-2-chloro-3-(methylsulfonylmethyl)pyridine (140 mg, 0.49 mmol, 94% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 8.63 (d, 1H), 8.21 (d, 1H), 4.70 (s, 2H), 3.10 (s, 3H); MS (EI) for C7H7BrClNO2S: 284, 286, 288 (Br+Cl isotopes, MH+).

Workup

  1. temperatureAfter cooling to rt
  2. extractionwas subsequently extracted twice with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-593fcaba36af44879fa0e4a56adbc78c
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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