Water → HCID 86650828, compound

HRID 447815Notes

Reaction equation

HRID 447815 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=O.Cl.[CH3:13][O:14][NH2:15].O>N1C=CC=CC=1>[CH3:13][O:14][N:15]=[CH:7][C:6]1[CH:9]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[S:10][CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 521874O-Methylhydroxylamine hydrochlorideHCID 16733861HCID 16733861, compound

Product 1

HCID 86650828HCID 86650828, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(Step 2) 5-Bromo-2-(methylsulfanyl)benzaldehyde obtained in Step 1 (11.0 g) and O-methylhydroxylamine hydrochloride (4.37 g) were stirred in pyridine (30 ml) at room temperature for 14 hr. The reaction solution was treated with water, and extracted with ethyl acetate. The extract was washed successively with 1N hydrochloric acid (twice) and saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give 5-bromo-2-(methylsulfanyl)benzaldehyde O-methyloxime (11.9 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed successively with 1N hydrochloric acid (twice) and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b3ff427e27884dd5bad00f40bdc7f835
Source dataset
uspto-grants-2013_07
Patent number
US08481569B2

Reaction notes

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