Ethyl bromoacetate → ethyl 2-(7-bromo-4-fluoro-9-hydroxy-2-methoxy-9H-xanthen-9-yl)acetate

HRID 455612노트

반응식

HRID 455612 반응식
BrBr.Br[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br:10][C:11]1[CH:24]=[C:23]2[C:14]([O:15][C:16]3[C:17]([F:28])=[CH:18][C:19]([O:26][CH3:27])=[CH:20][C:21]=3[C:22]2=[O:25])=[CH:13][CH:12]=1.C1COCC1>C(OCC)C.[Zn]>[Br:10][C:11]1[CH:24]=[C:23]2[C:14]([O:15][C:16]3[C:17]([F:28])=[CH:18][C:19]([O:26][CH3:27])=[CH:20][C:21]=3[C:22]2([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[OH:25])=[CH:13][CH:12]=1

참가 물질

7

반응물 4

HCID 7748Ethyl bromoacetateHCID 8028TetrahydrofuranHCID 24408BromineHCID 574756397-bromo-4-fluoro-2-methoxy-9H-xanthen-9-one

생성물 1

HCID 67383096ethyl 2-(7-bromo-4-fluoro-9-hydroxy-2-methoxy-9H-xanthen-9-yl)acetate수율 100%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 3283Diethyl Ether용매

실험 절차

Bromine (0.797 ml, 15.47 mmol) was added to a suspension of zinc dust (8.09 g, 124 mmol in diethyl ether (150 ml) at RT. After 5 minutes, ethyl 2-bromoacetate (6.86 ml, 61.9 mmol) was added drop wise over a time period of 20 minutes and the reaction mixture was heated to reflux for 2 hours. 7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-one (10 g, 30.9 mmol) was added in one portion, followed by THF (100 ml) and the reaction mixture was heated to reflux for 3 hours. The reaction mixture was quenched with aqueous saturated NH4Cl solution (100 mL) and EtOAc (100 mL) and stirred 2 hours at RT. The solution was filtered and the organic phase was separated. The solvent was removed under educed pressure to afford ethyl 2-(7-bromo-4-fluoro-9-hydroxy-2-methoxy-9H-xanthen-9-yl)acetate (12.7 g, 30.9 mmol, 100% yield).

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux for 3 hours
  5. customThe reaction mixture was quenched with aqueous saturated NH4Cl solution (100 mL) and EtOAc (100 mL)
  6. filtrationThe solution was filtered
  7. customthe organic phase was separated
  8. customThe solvent was removed

출처 및 근거

ORD 기록
ord-d3ddffbe941c464a8be890d712c32105
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497264B2

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