tert-Butyl acrylate → (E)-tert-Butyl 3-(6-acetyl-3-chloro-2-fluorophenyl)acrylate

HRID 63825노트

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HRID 63825 반응식
Br[C:2]1[C:7]([F:8])=[C:6]([Cl:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11].[C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:16])[CH:14]=[CH2:15]>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:10]([C:3]1[C:2](/[CH:15]=[CH:14]/[C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[C:7]([F:8])[C:6]([Cl:9])=[CH:5][CH:4]=1)(=[O:12])[CH3:11]

참가 물질

5

반응물 2

HCID 15458tert-Butyl acrylateHCID 666985481-(2-Bromo-4-chloro-3-fluorophenyl)ethanone

생성물 1

HCID 66698573(E)-tert-Butyl 3-(6-acetyl-3-chloro-2-fluorophenyl)acrylate수율 51%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

To a mixture of Intermediate 12C (50 g, 198 mmol), tert-butyl acrylate (50.9 g, 397 mmol) and TEA (55 mL, 397 mmol) in DMF (500 mL) was added Pd(OAc)2 (8.9 g, 39.7 mmol). The resulting mixture was stirred at 90° C. overnight. The reaction was cooled to rt, filtered, and the filtrate was concentrated. Purification by column chromatography gave Intermediate 12D (30 g, 51%) as a light yellow solid. MS (ESI) m/z: 242.7 (M+H)+.

후처리

  1. temperatureThe reaction was cooled to rt
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated
  4. customPurification by column chromatography

출처 및 근거

ORD 기록
ord-0565f12501f741388280d1e08d1bce89
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447110B2

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