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

HRID 1191615노트

반응식

HRID 1191615 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9887a326c81c447aaecb6c41ead45057
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680117B2

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