Diethyl Ether → (4-Chloro-3-fluoro-2-methoxyphenyl)[2-(trifluoromethyl)oxiranyl]methanone

HRID 1191615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1191615
[F:1][C:2]([F:7])([F:6])[CH:3]1[O:5][CH2:4]1.C([Li])CCC.[Cl:13][C:14]1[CH:25]=[CH:24][C:17]([C:18](N(OC)C)=[O:19])=[C:16]([O:26][CH3:27])[C:15]=1[F:28].C(OCC)C>C1COCC1.CCCCCC>[Cl:13][C:14]1[CH:25]=[CH:24][C:17]([C:18]([C:3]2([C:2]([F:7])([F:6])[F:1])[CH2:4][O:5]2)=[O:19])=[C:16]([O:26][CH3:27])[C:15]=1[F:28]

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 5207692-(Trifluoromethyl)oxiraneHCID 866305624-chloro-3-fluoro-2,N-dimethoxy-N-methylbenzamidHCID 178418339Butyllithium

Produkt 1

HCID 86630563(4-Chloro-3-fluoro-2-methoxyphenyl)[2-(trifluoromethyl)oxiranyl]methanoneAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel2×

Versuchsvorschrift

0.44 ml (5.1 mmol) 1,1,1-trifluoro-2,3-epoxypropane in 7.5 ml THF and 2.2 ml hexane are cooled to −100° C. and 2.03 ml of a 2.5 M n-butyl lithium solution (5.1 mmol) in hexane are added over 15 minutes while the temperature does not exceed −95° C. 10 minutes after complete addition 0.57 g (2.3 mmol) 4-chloro-3-fluoro-2, N-dimethoxy-N-methylbenzamid in 10 ml THF are added over 15 minutes while the temperature does not exceed −95° C. After 3 hours at −100° C. 2.3 ml diethyl ether is added and the reaction mixture is warmed to room temperature over 14 hours. The reaction is quenched by addition of saturated ammonium chloride solution. The phases were separated and the aqueous layer is extracted twice with diethyl ether, the combined organic phases washed with brine, dried over sodium sulphate and then evaporated to yield 570 mg of (4-chloro-3-fluoro-2-methoxyphenyl)[2-(trifluoromethyl)oxiranyl]methanone. 1H-NMR (CDCl3); δ=2.99 (dq, 1H), 3.37 (d, 1H), 4.14 (d, 3H), 7.18 (m, 1H), 7.19 (m, 1H).

Aufarbeitung

  1. customdoes not exceed −95° C
  2. additionare added over 15 minutes while the temperature
  3. customdoes not exceed −95° C
  4. customThe reaction is quenched by addition of saturated ammonium chloride solution
  5. customThe phases were separated
  6. extractionthe aqueous layer is extracted twice with diethyl ether
  7. washthe combined organic phases washed with brine
  8. dry with materialdried over sodium sulphate
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-9887a326c81c447aaecb6c41ead45057
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680117B2

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