Sodium Chloride → 5-Bromopyridine-3-sulfonyl chloride

HRID 558489Notes

Reaction equation

HRID 558489 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8]([OH:11])(=O)=[O:9])[CH:5]=[N:6][CH:7]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:13].P(Cl)(Cl)(Cl)=O.C([O-])(O)=O.[Na+].[Na+].[Cl-]>C(OC)(C)(C)C>[Br:1][C:2]1[CH:3]=[C:4]([S:8]([Cl:13])(=[O:11])=[O:9])[CH:5]=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 126842615-Bromopyridine-3-sulphonic acid

Product 1

HCID 203244745-Bromopyridine-3-sulfonyl chlorideYield 98.4%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A mixture of 5-bromo-pyridine-3-sulfonic acid (Example B.2 step 1) (7.14 g, 30 mmol), phosphorus pentachloride (9.68 g, 47 mmol) and phosphorus oxychloride (20 mL) was heated to reflux for 4 h (according to J. Org. Chem. 1989, 54(2), 389). The reaction mixture was concentrated to dryness to give a yellow semisolid, dissolved in ice water and tert-butyl-methyl-ether, and cautiously added sat. NaHCO3-sol. until neutralized, saturated with solid NaCl, separated phases, dried organic layer over Na2SO4. Removal of the solvent in vacuum gave the title compound as a yellow solid (7.57 g, 98%). MS (EI) 254.9 [(M)+], 256.9 [(M+2)+] and 258.9 [(M+4)+]; mp 64° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h (according to J. Org. Chem. 1989, 54(2), 389)
  3. concentrationThe reaction mixture was concentrated to dryness
  4. customto give a yellow semisolid
  5. customseparated phases, dried organic layer over Na2SO4
  6. customRemoval of the solvent in vacuum

Sources & evidence

ORD record
ord-b8facc8fe3b04f4fae5f28b0cb01461a
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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