Water → 2-Bromo-4-methoxy-3-(4-nitrophenoxy)benzaldehyde

HRID 131584ノート

反応式

HRID 131584 の反応式
[F-].[K+].[Br:3][C:4]1[C:11]([OH:12])=[C:10]([O:13][CH3:14])[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7].F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1.O>CS(C)=O>[Br:3][C:4]1[C:11]([O:12][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[C:10]([O:13][CH3:14])[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7]

参加物

6

反応物 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 2240112-BromoisovanillinHCID 522689Potassium Fluoride

生成物 1

HCID 211057062-Bromo-4-methoxy-3-(4-nitrophenoxy)benzaldehyde収率 65.4%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒3 回

反応条件

温度
140 °C

実験手順

To a stirred suspension of potassium fluoride (1.89 gm, 0.0326 mol) in dry DMSO (10 ml) was added a solution of 2-bromoisovanillin (5.0 gm, 0.0217 mol) in DMSO (10 ml). A solution of 4-fluoronitrobenzene (5.0 gm, 0.0260 mol) in DMSO (5 ml) was added to the above suspension and the reaction mixture was stirred at 140° C. for 4 h. The reaction mixture was cooled to room temperature and the contents were poured into water (150 ml) and extracted with ethyl acetate (50 ml×3). The organic extracts were combined and washed with 1N sodium hydroxide (25 ml×2), water and brine and dried over anhydrous sodium sulfate. The dried organic layer was concentrated in vacuo and the residue was purified by silica-gel column chromatography using 20% ethyl acetate-petroleum ether as the eluent to give 2-bromo-3-(p-nitrophenoxy)-4-methoxy benzaldehyde as a pale yellow solid (5.0 gm) mp: 132-140° C.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (50 ml×3)
  3. washwashed with 1N sodium hydroxide (25 ml×2), water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe dried organic layer was concentrated in vacuo
  6. customthe residue was purified by silica-gel column chromatography

出典と根拠

ORDレコード
ord-7a935dba3ce549eea48a1b6f1eb78cf0
出典データセット
uspto-grants-2008_06
特許番号
US07384962B2

反応ノート

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