5-Bromosalicylaldehyde → 2-Hydroxy-5-(methanesulfonyl)benzaldehyde

HRID 1920016Notes

Reaction equation

HRID 1920016 reaction equation
Br[C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.[CH3:11][S:12]([O-:14])=[O:13].[Na+]>CN1C(=O)CCC1.CCOC(C)=O.[Cu]I>[OH:10][C:5]1[CH:4]=[CH:3][C:2]([S:12]([CH3:11])(=[O:14])=[O:13])=[CH:9][C:6]=1[CH:7]=[O:8]

Participants

6

Reactant 2

HCID 728635-BromosalicylaldehydeHCID 2733271Sodium methanesulfinate

Product 1

HCID 574198652-Hydroxy-5-(methanesulfonyl)benzaldehyde

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

5-Bromosalicylaldehyde (0.402 g, 2.0 mmol), sodium methanesulfinate (0.918 g, 9.0 mmol), and copper(I) iodide (1.71 g, 9.0 mmol) were combined in NMP (16 mL) and stirred under N2 at 140° C. overnight. The mixture was diluted with 1:1 EtOAc:hexanes (150 mL) and filtered through a pad of Celite. The filtrate was washed three times with H2O, and then dried, filtered, and concentrated. The residue was purified by silica gel chromatography (0-100% EtOAc in hexanes) to give the title compound.

Workup

  1. filtrationhexanes (150 mL) and filtered through a pad of Celite
  2. washThe filtrate was washed three times with H2O
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1698f067d36a4612abd8ced75aad5912
Source dataset
uspto-grants-2012_05
Patent number
US08168678B2

Reaction notes

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