Dimethylformamide → 4-Chloro-2-fluoro-5-(pentyloxycarbonylmethyloxy)nitrobenzene

HRID 704089

反応式

HRID 704089 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Cl[CH2:25][C:26]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:27]>O>[Cl:1][C:2]1[C:3]([O:12][CH2:25][C:26]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:27])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([F:8])[CH:7]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 138488Acetic acid, chloro-, pentyl esterHCID 158655Phenol, 2-chloro-4-fluoro-5-nitro-

生成物 1

HCID 146178494-Chloro-2-fluoro-5-(pentyloxycarbonylmethyloxy)nitrobenzene収率 77.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

A mixture of 2-chloro-4-fluoro-5-nitrophenol (100 g), anhydrous potassium carbonate (86.6 g) and dimethylformamide (500 g) was heated at 50° C., and amyl 2-chloroacetate (90.2 g) was dropwise added thereto in 30 minutes, followed by allowing to stand at 60° C. for 4 hours. The reaction mixture was cooled to room temperature, and water (1500 g) was added thereto, followed by extraction with ethyl acetate (1500 g). The organic layer was separated, washed with water and concentrated under reduced pressure. The residue was distilled under reduced pressure to give 4-chloro-2-fluoro-5-(pentyloxycarbonylmethyloxy)nitrobenzene (Compound (III)) (129 g) as a pale yellow oil. Yield, 77%. b.p., 160°-165° C./0.7 mmHg.

後処理

  1. waitto stand at 60° C. for 4 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionfollowed by extraction with ethyl acetate (1500 g)
  4. customThe organic layer was separated
  5. washwashed with water
  6. concentrationconcentrated under reduced pressure
  7. distillationThe residue was distilled under reduced pressure

出典と根拠

ORDレコード
ord-4e61f74ca11c4edcacad9de6e4ffc51c
出典データセット
uspto-grants-1991_01
特許番号
US04985570

関連ノート

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