Sodium Sulfite → HCID 54520011, compound

HRID 862063Notes

Reaction equation

HRID 862063 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:16])=[C:6]([CH:15]=1)[CH:7]([OH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.ClC1C=CC=C(C(OO)=[O:25])C=1.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:16])=[C:6]([CH:15]=1)[CH:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N+:9]=1[O-:25])[OH:14]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 54260670HCID 54260670, compound

Product 1

HCID 54520011HCID 54520011, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5-bromo-2-hydroxy-α-(2-pyridyl)-benzyl alcohol (3.18 g) in chloroform (60 ml) was added at 0° C. 70% m-chloroperbenzoic acid (3.30 g). The mixture was stirred for 10 minutes at the same temperature, then for further 3.5 hours while warming up to room temperature. The reaction mixture was poured into an aqueous solution of sodium sulfite, followed by extraction with ethyl acetate. The extract solution was washed with an aqueous solution of sodium carbonate and a saturated aqueous saline solution, successively, dried (anhydrous sodium sulfate), and concentrated. The concentrate was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane) to give 2-(5-bromo-2, α-dihydroxybenzyl)pyridine N-oxide (2.50 g, m.p.188°-189° C.), whose spectrum data are shown below.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract solution was washed with an aqueous solution of sodium carbonate
  3. dry with materiala saturated aqueous saline solution, successively, dried (anhydrous sodium sulfate)
  4. concentrationconcentrated
  5. customThe concentrate was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1ea21d0adbd34eacbf7fd25d6a1c1f3a
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

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