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

HRID 897464

反応式

HRID 897464 の反応式
[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

参加物

5

反応物 2

HCID 70304-BromobenzophenoneHCID 443297Hydroxyamine hydrochloride

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 1049Pyridine溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-465b726311b6481b98bef0f2a57db009
出典データセット
uspto-grants-2005_07
特許番号
US06921763B2

関連ノート

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