4,4'-Difluorobenzophenone → HCID 22485640, compound

HRID 2181129Notes

Reaction equation

HRID 2181129 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=O)=[CH:4][CH:3]=1.Cl.[O:18]([NH2:20])[CH3:19]>C(O)C.N1C=CC=CC=1.C(OCC)(=O)C>[CH3:19][O:18][N:20]=[C:6]([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[C:5]1[CH:15]=[CH:16][C:2]([F:1])=[CH:3][CH:4]=1

Participants

6

Reactant 2

HCID 95824,4'-DifluorobenzophenoneHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 22485640HCID 22485640, compoundYield 99.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4,4′-difluorobenzophenone (3.00 g, 13.75 mmol) in a mixture of ethanol (10 ml) and pyridine (10 ml) was treated with methoxylamine hydrochloride (1.8 g, 21.7 mmol) and the resulting mixture was heated under reflux for 1 h. The cooled reaction mixture was diluted with ethyl acetate, washed successively with water, 1 N hydrochloric acid, saturated sodium bicarbonate and brine. After drying over anhydrous magnesium sulphate, evaporation of the solvent yielded 3.38 g (99% yield) of the title oxime ether as a clear syrup. 1HNMR 400 MHz (CDCl3) δ (ppm): 3.94 (3H, s, OCH3), 7.04 (2H, m, aromatics), 7.12 (2H, m, aromatics), 7.34 (2H, m, aromatics), 7.45 (2H, m, aromatics).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 1 h
  3. customThe cooled reaction mixture
  4. washwashed successively with water, 1 N hydrochloric acid, saturated sodium bicarbonate and brine
  5. dry with materialAfter drying over anhydrous magnesium sulphate, evaporation of the solvent

Sources & evidence

ORD record
ord-2dfea178b8d749698a9aaf4cb7f3523a
Source dataset
uspto-grants-2005_05
Patent number
US06890942B2

Reaction notes

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