Hydroxylamine → 2-Bromo-4-chloro-6-fluorobenzaldehyde oxime
Reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([F:11])[C:3]=1[CH:4]=O.[NH2:12][OH:13].O>CC(O)C>[Br:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([F:11])[C:3]=1[CH:4]=[N:12][OH:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
To a solution of 2-bromo-4-chloro-6-fluoro-benzaldehyde (15 g, 63.16 mmol) in 2-propanol (130 ml) was added hydroxylamine (50% solution in water, 4.55 g, 68.90 mmol) at 25° C. and the mixture was warmed to 40° C. for 2 h. Water (55 ml) was then added slowly to this mixture and the slurry was aged for 1 h at 20° C. The reaction mixture was filtered and the remaining solid was washed with a mixture of 2-propanol and water (1.5:1) and dried under vacuum to yield the title compound (12.5 g, 77%) as white solid.
Workup
- filtrationThe reaction mixture was filtered
- washthe remaining solid was washed with a mixture of 2-propanol and water (1.5:1)
- customdried under vacuum
Sources & evidence
- ORD record
- ord-664f97abdb2b4ccfa812b43145cecc9f
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08592426B2
Reaction notes
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