4-Bromobenzophenone → HCID 85578976, compound

HRID 432171Notes

Reaction equation

HRID 432171 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.[O:17]([NH2:19])[CH3:18]>C(O)C.N1C=CC=CC=1>[CH3:18][O:17][N:19]=[C:6]([C:5]1[CH:14]=[CH:15][C:2]([Br:1])=[CH:3][CH:4]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 70304-BromobenzophenoneHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 85578976HCID 85578976, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

A mixture of 4-bromobenzophenone (3.02 g, 0.0116 mol) and methoxylamine hydrochloride (4.83 g, 0.0578 mol) was heated in a mixture of ethanol (90 mL) and pyridine (18 mL) at reflux for 2 hours under an atmosphere of nitrogen. The solvents were removed under reduced pressure and the residue was partitioned between water (150 mL) and dichloromethane (100 mL). The water phase was further extracted twice with dichloromethane (80 mL each) and the combined organic extracts were dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash chromatography on silica gel using ethyl acetate/n-heptane (2:98) as mobile phase to yield (4-bromophenyl)(phenyl)methanone O-methyloxime as a colorless oil (3.13 g, 0.0108 mol): 1H NMR (DMSO-d6, 400 MHz) 7.67 (d, 1H), 7.59 (d, 1H), 7.48 (m, 4H), 7.32 (m, 1H), 7.26 (m, 2H), 3.93 (s, 3H) TLC (ethyl acetate/heptane 1:9) Rf 0.44.

Workup

  1. temperatureat reflux for 2 hours under an atmosphere of nitrogen
  2. customThe solvents were removed under reduced pressure
  3. customthe residue was partitioned between water (150 mL) and dichloromethane (100 mL)
  4. extractionThe water phase was further extracted twice with dichloromethane (80 mL each)
  5. dry with materialthe combined organic extracts were dried over magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-bb5e12589afe49ddb073bd983198196b
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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