Hydroxyamine hydrochloride → 1-(4-Bromo-2-hydroxy-phenyl)-2,2,2-trifluoro-ethanone oxime

HRID 1908233Notes

Reaction equation

HRID 1908233 reaction equation
C([O-])(=O)C.[Na+].Cl.[NH2:7][OH:8].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=O)[C:17]([F:20])([F:19])[F:18])=[C:12]([OH:22])[CH:11]=1>CO>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[N:7][OH:8])[C:17]([F:20])([F:19])[F:18])=[C:12]([OH:22])[CH:11]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 686299211-(4-Bromo-2-hydroxyphenyl)-2,2,2-trifluoroethan-1-one

Product 1

HCID 1363384541-(4-Bromo-2-hydroxy-phenyl)-2,2,2-trifluoro-ethanone oxime

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
64 °C

Procedure

To a round bottom flask were added sodium acetate (9.46 g, 115 mmol), hydroxylamine hydrochloride (7.09 g, 102 mmol) and MeOH (10 mL). To this mixture was added a solution consisting of 1-(4-bromo-2-hydroxy-phenyl)-2,2,2-trifluoro-ethanone (2.5 g, 9.3 mmol) and MeOH (62 mL). The reaction vessel was heated at 64° C. for 7 h before cooling to rt and pouring the reaction mixture into ice water (100 mL). The aqueous solution was then extracted with EtOAc (75 mL×2) and the organic layers dried (Na2SO4) and concentrated to yield the title compound as a mixture of the two possible oxime isomers (2.64 g, 100%).

Workup

  1. additionTo this mixture was added a solution
  2. temperaturebefore cooling to rt
  3. extractionThe aqueous solution was then extracted with EtOAc (75 mL×2)
  4. dry with materialthe organic layers dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-44885f25e5fd46ca8b31e5410c47bf48
Source dataset
uspto-grants-2013_12
Patent number
US08598202B2

Reaction notes

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