Water → 5-Bromo-6-chloro-pyridine-3-sulphenic acid

HRID 723079Notes

Reaction equation

HRID 723079 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=O)=[O:10])[CH:5]=[N:6][C:7]=1[Cl:8].S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+].O>CCO>[Br:1][C:2]1[CH:3]=[C:4]([S:9][OH:10])[CH:5]=[N:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 962WaterHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 27936265-Bromo-6-chloropyridine-3-sulfonyl chloride

Product 1

HCID 218865015-Bromo-6-chloro-pyridine-3-sulphenic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Bromo-6-chloro-pyridine-3-sulfonyl chloride (2.5 g, 8.6 mmol), sodium sulfite (2.0 g, 16.1 mmol), and sodium bicarbonate (1.4 g, 16.9 mmol) were dissolved into water (8 mL) and EtOH (3 mL). The reaction mixture was allowed to stir at RT for 12 hours. TLC analysis showed loss of SM and formation of a very polar new spot. Reaction mixture was concentrated in vacuo resulting in a white solid and was used without further purification. ESI-MS (m/z): Calcd. for C5H3BrClNO2S: 255.8 (M+H); found: 256.0. 1H-NMR (CD3OD): δ 8.55 (m, 1H), 8.29 (m, 1H).

Workup

  1. customReaction mixture
  2. concentrationwas concentrated in vacuo
  3. customresulting in a white solid
  4. customwas used without further purification

Sources & evidence

ORD record
ord-23d157d5bcc14c7e8e759956166ee6df
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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