Hydroxyamine hydrochloride → 1-(2-Bromophenyl)propan-2-one oxime

HRID 475111Notes

Reaction equation

HRID 475111 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9](=O)[CH3:10].CC([O-])=O.[Na+].Cl.[NH2:18][OH:19]>CO>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9](=[N:18][OH:19])[CH3:10]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 27340921-(2-Bromophenyl)propan-2-one

Product 1

HCID 866946991-(2-Bromophenyl)propan-2-one oximeYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 1-(2-bromophenyl)propan-2-one (1.5 g, 7.04 mmol) and NaOAc (693 mg, 8.45 mmol) in MeOH (50 mL) at RT was added hydroxylamine hydrochloride (539 mg, 7.8 mmol). After the reaction mixture was stirred at RT for 18 h, it was concentrated in vacuo. Water was added (100 mL), and the mixture was extracted with EtOAc (50 mL×3), dried (MgSO4) and concentrated in vacuo to afford 1-(2-bromophenyl)propan-2-one oxime as a yellow solid (1.51 g, 94%). MS (ESI): m/z=228.1 [M+1]+.

Workup

  1. concentrationit was concentrated in vacuo
  2. additionWater was added (100 mL)
  3. extractionthe mixture was extracted with EtOAc (50 mL×3)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cf554ec425784c5488491af913c1a488
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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