Bromocyclopentane → N-[4-Chloro-5-(cyclopentyloxy)-2-fluorophenyl]carbamic acid ethyl ester

HRID 128540

반응식

HRID 128540 반응식
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[NH:10][C:11](=[O:15])[O:12][CH2:13][CH3:14].C(=O)([O-])[O-].[K+].[K+].[CH:22]1(Br)[CH2:26][CH2:25][CH2:24][CH2:23]1>C(#N)C>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:4][C:3]=1[NH:10][C:11](=[O:15])[O:12][CH2:13][CH3:14]

참가 물질

5

반응물 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 19374480Ethyl (4-chloro-2-fluoro-5-hydroxyphenyl)carbamate

생성물 1

HCID 11033971N-[4-Chloro-5-(cyclopentyloxy)-2-fluorophenyl]carbamic acid ethyl ester수율 98.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Then, a solution of the resulting ethyl N-(2-fluoro-4-chloro-5-hydroxyphenyl)carbamate (10.0 g, 42.8 mmol) and potassium carbonate (8.87 g, 64.2 mmol) in acetonitrile (150 ml) was stirred for 1 hour at 80° C. Then, cyclopentyl bromide (9.57 g, 84.2 mmol) was added dropwise thereto, followed by reacting for further 7 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was made acidic by adding 1N hydrochloric acid (100 ml) and extracted with ethyl acetate (100 ml×8 times). The organic layer was washed with water, dried, and the solvent was distilled off under reduced pressure to obtain ethyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamate (12.7 g, 98% yield).

후처리

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionby adding 1N hydrochloric acid (100 ml)
  4. extractionextracted with ethyl acetate (100 ml×8 times)
  5. washThe organic layer was washed with water
  6. customdried
  7. distillationthe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-bc7dca1b17c34392807cc7113697d400
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05464811

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