Hydrochloric Acid → (2Z)-1-(4-bromophenyl)-2-hydroxyiminopentan-1-one

HRID 80395Notes

Reaction equation

HRID 80395 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:14])[CH2:10][CH2:11][CH2:12][CH3:13])=[CH:5][CH:4]=1.[N:15]([O-])=[O:16].[Na+]>C1COCC1.C(OCC)C>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([C:9](=[O:14])/[C:10](=[N:15]\[OH:16])/[CH2:11][CH2:12][CH3:13])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 817174'-BromovalerophenoneHCID 23668193Sodium Nitrite

Product 1

HCID 87519930(2Z)-1-(4-bromophenyl)-2-hydroxyiminopentan-1-oneYield 59.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

The conc. HCl (40 mL) was added dropwise to a solution of 1-(4-bromophenyl)pentan-1-one (4.68 g, 19.41 mmol) and sodium nitrite (4.02 g, 58.2 mmol) in THF (80 ml) at 0° C. and allowed to warm to room temperature and stirred 18 hours. The reaction mixture was diluted with diethyl ether and the organic phase washed with sat'd NaHCO3 and brine. Concentration gave (Z)-1-(4-bromophenyl)-2-(hydroxyimino)pentan-1-one 3.1 g (33%) as an oil which was used without further purification.). RT=2.1 min, (Condition 1) LCMS: Anal. Calcd. for C11H12BrN1O2 270.01; found: 270.15 (M+H)+.

Workup

  1. washthe organic phase washed with sat'd NaHCO3 and brine
  2. concentrationConcentration

Sources & evidence

ORD record
ord-c68d9d439ced4844823de55c75c3ac2e
Source dataset
uspto-grants-2014_09
Patent number
US08846023B2

Reaction notes

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