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Hydroxylamine → 2-Bromo-4-chloro-6-fluorobenzaldehyde oxime

HRID 2046565
Notes
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Reaction equation

HRID 2046565 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 962WaterHCID 707011832-Bromo-4-chloro-6-fluorobenzaldehyde

Product 1

HCID 866672572-Bromo-4-chloro-6-fluorobenzaldehyde oximeYield 78.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
40 °C
On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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

  1. filtrationThe reaction mixture was filtered
  2. washthe remaining solid was washed with a mixture of 2-propanol and water (1.5:1)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-664f97abdb2b4ccfa812b43145cecc9f
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08592426B2

Reaction notes

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