Bromine → 2-Isopropylsulphinylbenzaldehyde

HRID 1928562Notes

Reaction equation

HRID 1928562 reaction equation
[CH:1]([S:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=[O:8])([CH3:3])[CH3:2].BrBr.[O-:15]S([O-])=O.[Na+].[Na+]>ClCCl>[CH:1]([S:4]([C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=[O:8])=[O:15])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24408BromineHCID 24437Sodium SulfiteHCID 112061372-(Isopropylthio)benzaldehyde

Product 1

HCID 598415842-Isopropylsulphinylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(isopropylthio)benzaldehyde (0.33 g, 1.83 mmol) in dichloromethane (10 ml) was admixed with aqueous KHCO3 solution (1.18 g in 10 ml of H2O). With vigorous stirring, a solution of bromine (0.310 g, 1.93 mmol) in dichloromethane (1.5 ml) was added dropwise. After continuing to stir for 20 min, a spatula-tip of Na2SO3 was added, and the organic phase was removed, washed with saturated NaCl solution, dried over MgSO4 and filtered, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (3:1 to 1:1 hexane:ethyl acetate). The product precipitated out as a yellowish oil. Yield 0.304 g (85%).

Workup

  1. customthe organic phase was removed
  2. washwashed with saturated NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (3:1 to 1:1 hexane:ethyl acetate)
  7. customThe product precipitated out as a yellowish oil

Sources & evidence

ORD record
ord-cbae1d996ed64f209cb2b016cb6a8f15
Source dataset
uspto-grants-2012_05
Patent number
US08183382B2

Reaction notes

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