Water → 4-Bromo-3-methylbenzaldehyde oxime

HRID 216001Notes

Reaction equation

HRID 216001 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[CH3:10].Cl.[NH2:12][OH:13].C([O-])(=O)C.[Na+].O>C(O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[N:12][OH:13])=[CH:4][C:3]=1[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 109215214-Bromo-3-methylbenzaldehyde

Product 1

HCID 738479544-Bromo-3-methylbenzaldehyde oximeYield 78.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-bromo-3-methyl-benzaldehyde (4.3 g) (Example I1) in ethanol (50 ml), were added at ambient temperature hydroxylamine hydrochloride (1.75 g), sodium acetate (2.07 g) and water (15 ml). The reaction mixture was stirred at ambient temperature for 3 hours. The reaction mixture was concentrated and the residue partitioned between ethyl acetate and aqueous sodium hydroxide (2M). The phases were separated and the organic phase was washed with brine, dried over sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 4:1) to give 4-bromo-3-methyl-benzaldehyde oxime (3.65 g) as a white solid. 1H-NMR (400 MHz, CDCl3): 8.05 (s, 1H), 7.50 (m, 2H), 7.25 (d, 1H), 2.40 (s, 3H) ppm.

Workup

  1. customwere added at ambient temperature
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue partitioned between ethyl acetate and aqueous sodium hydroxide (2M)
  4. customThe phases were separated
  5. washthe organic phase was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-0c33f4b2a5db4b569b6a160e54dbc67b
Source dataset
uspto-grants-2012_06
Patent number
US08193221B2

Reaction notes

Loading…