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Boron tribromide → Ethyl {3-chloro-4-[4-(ethyloxy)-9-hydroxy-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]phenyl}acetate

HRID 222433
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HRID 222433 반응식
[CH2:1]([O:3][C:4](=[O:39])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:20](=[O:21])[C:19]3[C:18]([O:22][CH2:23][C:24]4C=CC=CC=4)=[C:17]4[CH:30]=[CH:31][CH:32]=[CH:33][C:16]4=[C:15]([O:34]CC)[C:14]=3[C:13]2=[O:37])=[C:8]([Cl:38])[CH:7]=1)[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[Cl:38][C:8]1[CH:7]=[C:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:39])[CH:11]=[CH:10][C:9]=1[N:12]1[C:13](=[O:37])[C:14]2[C:15]([OH:34])=[C:16]3[CH:33]=[CH:32][CH:31]=[CH:30][C:17]3=[C:18]([O:22][CH2:23][CH3:24])[C:19]=2[C:20]1=[O:21]
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참가 물질

4

반응물 2

HCID 25134Boron tribromide2회HCID 58231507ethyl (3-chloro-4-{4-(ethyloxy)-1,3-dioxo-9-[(phenylmethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetate

생성물 1

HCID 58012488Ethyl {3-chloro-4-[4-(ethyloxy)-9-hydroxy-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]phenyl}acetate수율 63%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
-78 °C

실험 절차

To a solution of ethyl(3-chloro-4-{4-(ethyloxy)-1,3-dioxo-9-[(phenylmethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetate (1.75 g, 3.22 mmol) in DCM (40 ml), cooled to −78° C. under an atmosphere of argon, was added boron tribromide (0.31 ml, 3.22 mmol) drop wise. Stirred at −78° C. for 12 minutes. A further addition of boron tribromide (0.31 ml, 3.22 mmol) was made drop wise. The reaction mixture was quenched with water and warmed to room temperature. This was extracted twice with DCM using a hydrophobic frit. The organic phase was evaporated to an yellow solid. This was purified by chromatography on silica gel, eluting with ethyl acetate (0-60%) in hexane to give the title compound as a orange oily solid (0.920 g, 2.03 mmol). LC/MS: Rt=3.65, [MH]+ 454.

후처리

  1. customThe reaction mixture was quenched with water
  2. temperaturewarmed to room temperature
  3. extractionThis was extracted twice with DCM using a hydrophobic frit
  4. customThe organic phase was evaporated to an yellow solid
  5. customThis was purified by chromatography on silica gel
  6. washeluting with ethyl acetate (0-60%) in hexane

출처 및 근거

ORD 기록
ord-42925e32dd504d1dbfb7dd5eab39b232
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08207213B2

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