4-Bromobenzophenone → Methanone, (4-bromophenyl)phenyl-, oxime

HRID 432174

Reaction equation

HRID 432174 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=O)=[CH:4][CH:3]=1.Cl.[NH2:17][OH:18]>C(O)C.N1C=CC=CC=1>[Br:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:17][OH:18])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 70304-BromobenzophenoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 3484095Methanone, (4-bromophenyl)phenyl-, oximeYield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

A mixture of 4-bromobenzophenone (10.0 g, 0.0383 mol) and hydroxylamine hydrochloride (13.3 g, 0.192 mol) was heated in a mixture of ethanol (250 mL) and pyridine (50 mL) at reflux for 2 hours under an atmosphere of nitrogen. The solvents were removed under the reduced pressure and the residue was partitioned between water (300 mL) and dichloromethane (300 mL). The water phase was further extracted with dichloromethane twice (180 mL each) and the combined organic extracts were dried over magnesium sulfate. The solvent was removed under the reduced pressure and the residue was purified by flash chromatography on silica gel using ethyl acetate/n-heptane (1:9) as mobile phase to yield (4-bromophenyl)(phenyl)methanone oxime as a white solid (9.93 g, 0.036 mol): 1H NMR (DMSO-d6, 400 MHz) 7.66 (d, 1H), 7.57(d, 1H), 7.33 (m, 7H) TLC (ethyl acetate/heptane 1:5) Rf 0.38.

Workup

  1. temperatureat reflux for 2 hours under an atmosphere of nitrogen
  2. customThe solvents were removed under the reduced pressure
  3. customthe residue was partitioned between water (300 mL) and dichloromethane (300 mL)
  4. extractionThe water phase was further extracted with dichloromethane twice (180 mL each)
  5. dry with materialthe combined organic extracts were dried over magnesium sulfate
  6. customThe solvent was removed under the reduced pressure
  7. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-39ddb03b9c46492691c90b2cc51d6b71
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Linked notes

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