Potassium Carbonate → 2-Fluoro-4-chloro-5-cyclopentyloxynitrobenzene

HRID 21474

반응식

HRID 21474 반응식
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC(S(O[CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)(=O)=O)=CC=1>C(#N)C>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 158655Phenol, 2-chloro-4-fluoro-5-nitro-HCID 317685Cyclopentyl 4-methylbenzene-1-sulfonate

생성물 1

HCID 193744702-Fluoro-4-chloro-5-cyclopentyloxynitrobenzene수율 92.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of 2-fluoro-4-chloro-5-hydroxynitrobenzene (7.1 g, 37.1 mmol) and potassium carbonate (5.1 g, 37.1 mmol) in acetonitrile (300 ml) was stirred for 2 hours at a refluxing temperature. Cyclopentyl p-toluenesulfonate (10.3 g, 40.8 mmol) was added thereto, followed by stirring further for 2 hours under refluxing. After completion of the reaction, the solvent was distilled off under reduced pressure from the reaction mixture, in hydrochloric acid (300 ml) was added thereto, and the mixture was extracted with ethyl acetate (100 ml×3 times). The organic layer was washed with an aqueous solution of sodium bicarbonate and water, dried, and the solvent was distilled off under reduced pressure to obtain 2-fluoro-4-chloro-5-cyclopentyloxynitrobenzene as a yellow solid (8.93 g, 34.3 mmol, 92.6% yield).

후처리

  1. temperatureunder refluxing
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure from the reaction mixture, in hydrochloric acid (300 ml)
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate (100 ml×3 times)
  6. washThe organic layer was washed with an aqueous solution of sodium bicarbonate and water
  7. customdried
  8. distillationthe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-0b1ea39f652a4ec0b1ad722b5587f73d
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424277

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