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

HRID 128540

Reaktionsgleichung

Reaktionsgleichung von HRID 128540
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 11033971N-[4-Chloro-5-(cyclopentyloxy)-2-fluorophenyl]carbamic acid ethyl esterAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-bc7dca1b17c34392807cc7113697d400
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05464811

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