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

HRID 704089

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HRID 704089 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4e61f74ca11c4edcacad9de6e4ffc51c
출처 데이터셋
uspto-grants-1991_01
특허 번호
US04985570

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