Azobisisobutyronitrile → (E)-3-[2-Bromomethyl-6-(3-ethoxycarbonylpropoxy)phenyl]acrylic acid ethyl ester

HRID 420342노트

반응식

HRID 420342 반응식
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1/[CH:16]=[CH:17]/[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:2].[Br:24]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>ClC1C=CC=CC=1.O>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][Br:24])[C:10]=1/[CH:16]=[CH:17]/[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:2]

참가 물질

6

반응물 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 575864834-[2-((E)-2-ethoxycarbonyl-vinyl)-3-methyl-phenoxy]-butyric acid ethyl ester

생성물 1

HCID 57586460(E)-3-[2-Bromomethyl-6-(3-ethoxycarbonylpropoxy)phenyl]acrylic acid ethyl ester수율 71.2%

시약·촉매·용매 2

HCID 962Water용매HCID 7964Chlorobenzene용매

반응 조건

온도
85 °C

실험 절차

To a solution of 4-[2-((E)-2-ethoxycarbonyl-vinyl)-3-methyl-phenoxy]-butyric acid ethyl ester (8.0 g, 25.0 mmol) in chlorobenzene (190 mL) were added N-bromosuccinimide (6.67 g, 37.5 mmol) and 2,2′-azobisisobutyronitrile (AIBN) (591 mg, 3.6 mmol) at room temperature. Then, the solution was heated to 85° C. and stirred for 1 h. Then, the reaction mixture was cooled to room temperature and diluted with water (100 mL). Then, the organic compound was extracted into hexanes (3×100 mL). The combined organic extracts were washed with brine solution (150 mL) and the organic solution was dried over anhydrous magnesium sulfate. Filtration of the drying agent and the removal of the solvent gave a crude oil. The crude oil was purified by using a Biotage (40L) column eluting with 15-25% ethyl acetate in hexanes to isolate 4-[3-bromomethyl-2-((E)-2-ethoxycarbonyl-vinyl)-phenoxy]-butyric acid ethyl ester (7.11 g, 71%) as a low melting solid: ES(+)-HRMS m/e calculated for C18H23BrO5 (M+Na)+ 421.0621, found 421.0621.

후처리

  1. temperatureThen, the reaction mixture was cooled to room temperature
  2. extractionThen, the organic compound was extracted into hexanes (3×100 mL)
  3. washThe combined organic extracts were washed with brine solution (150 mL)
  4. dry with materialthe organic solution was dried over anhydrous magnesium sulfate
  5. filtrationFiltration of the drying agent
  6. customthe removal of the solvent
  7. customgave a crude oil
  8. customThe crude oil was purified
  9. washeluting with 15-25% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-c6bed806a04a443681bbe8167abda6e8
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093385B2

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