Sodium Bicarbonate → (4-(Methylsulfinyl)phenyl)boronic acid

HRID 1708053Notes

Reaction equation

HRID 1708053 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([B:9]([OH:11])[OH:10])=[CH:5][CH:4]=1.C(=O)(O)[O-:13].[Na+]>C(#N)C.O>[CH3:1][S:2]([C:3]1[CH:4]=[CH:5][C:6]([B:9]([OH:11])[OH:10])=[CH:7][CH:8]=1)=[O:13]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 27339594-(Methylthio)phenylboronic acid

Product 1

HCID 2773531(4-(Methylsulfinyl)phenyl)boronic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A solution of [4-(methylthio)phenyl]boronic acid (1.008 g) in acetonitrile (60 ml) and water (6 ml) was cooled with a dry ice-acetone bath until it just began to freeze. A solution of ceric ammonium nitrate (6.72 g) in water (10 ml) was added with swirling. The resulting solution was left to warm to room temperature. The mixture was then basified to pH5 by addition of 8% aqueous sodium bicarbonate (16 ml) and evaporated to dryness by re-evaporation with absolute ethanol. The dried residue was purified by SPC (Merck 7729) using ethyl acetate-ethanol (9:1 followed by 4:1 and 7:3) as eluent, to give a colourless solid. The solid was further purified by FCC eluting with dichloromethane:ethanol (9:1) to give the title compound (1.00 g) as a colourless gum.

Workup

  1. waitThe resulting solution was left
  2. customevaporated to dryness by re-evaporation with absolute ethanol
  3. customThe dried residue was purified by SPC (Merck 7729)
  4. customto give a colourless solid
  5. customThe solid was further purified by FCC
  6. washeluting with dichloromethane:ethanol (9:1)

Sources & evidence

ORD record
ord-9fd814a5c77a44f1833a60e2c7ce6128
Source dataset
uspto-grants-1994_10
Patent number
US05356893

Reaction notes

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