Water → HCID 86650828, compound

HRID 1013968Notes

Reaction equation

HRID 1013968 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-beb2c1e34c1d4c5487d37da6937d7077
Source dataset
uspto-grants-2011_07
Patent number
US07982044B2

Reaction notes

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