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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
ノート
印刷プレビュー

反応式

HRID 222433 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 25134Boron tribromide2 回HCID 58231507ethyl (3-chloro-4-{4-(ethyloxy)-1,3-dioxo-9-[(phenylmethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetate

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-42925e32dd504d1dbfb7dd5eab39b232
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08207213B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート