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Ethyl Acetate → 5-Bromo-7-chloro-2-(4-phenoxy-benzyl)-2,3-dihydro-isoindol-1-one

HRID 2427646
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HRID 2427646 반응식
CO[C:3](=[O:14])[C:4]1[C:9]([Cl:10])=[CH:8][C:7]([Br:11])=[CH:6][C:5]=1[CH2:12]Br.[O:15]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[Br:11][C:7]1[CH:6]=[C:5]2[C:4](=[C:9]([Cl:10])[CH:8]=1)[C:3](=[O:14])[N:27]([CH2:26][C:25]1[CH:28]=[CH:29][C:22]([O:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:23][CH:24]=1)[CH2:12]2
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참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2760343(4-Phenoxyphenyl)methanamineHCID 59512234Methyl 4-bromo-2-(bromomethyl)-6-chlorobenzoate

생성물 1

HCID 579496705-Bromo-7-chloro-2-(4-phenoxy-benzyl)-2,3-dihydro-isoindol-1-one수율 32%

시약·촉매·용매 2

HCID 1140
Toluene
용매
HCID 8058Hexane용매

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온도
100 °C

실험 절차

A mixture of 4-bromo-2-bromomethyl-6-chloro-benzoic acid methyl ester (0.492 g, 1.6 mmol), 4-phenoxy-benzylamine (0.256 mL, 2.0 mmol), and K2CO3 (0.414 g, 3 mmol) in toluene (5 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 5-bromo-7-chloro-2-(4-phenoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.200 g, 32%). GC-MS: m/z 429 (M)+, 336 (M−93)+.

후처리

  1. temperaturewas heated

출처 및 근거

ORD 기록
ord-6adebd7f661841dc813f920840c21b9f
출처 데이터셋
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07968570B2

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