Water → 4-fluoro-2-methylsulfanyl-benzaldehyde-O-methyl-oxime

HRID 2214684Notes

Reaction equation

HRID 2214684 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([S:10][CH3:11])[CH:3]=1.Cl.[CH3:13][O:14][NH2:15].C([O-])(=O)C.[Na+].O>CCOCC.C1COCC1>[CH3:13][O:14][N:15]=[CH:6][C:5]1[CH:8]=[CH:9][C:2]([F:1])=[CH:3][C:4]=1[S:10][CH3:11]

Participants

7

Reactant 4

HCID 962WaterHCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 219474094-Fluoro-2-(methylthio)benzaldehyde

Product 1

HCID 865927644-fluoro-2-methylsulfanyl-benzaldehyde-O-methyl-oximeYield 99%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 250 mL round bottom flask was charged with 4-fluoro-2-methylsulfanylbenzaldehyde (5.106 g, 30 mmol), O-methylhydroxylamine hydrochloride (3.758 g, 45 mmol), sodium acetate (6.124 g, 45 mmol), water (50 mL) and THF (75 mL). The reaction mixture was stirred at room temperature for 4 h and taken up into ether (300 mL), washed with water (2×50 mL) and brine (50 mL). The organic phase was dried over anhydrous Na2SO4, filtered and concentrated to give 4-fluoro-2-methylsulfanyl-benzaldehyde-O-methyl-oxime (5.892 g, 99%) as a white solid.

Workup

  1. washwashed with water (2×50 mL) and brine (50 mL)
  2. dry with materialThe organic phase was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b2c88be83822457aa0670355eed6f7bc
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

Loading…