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Hydrochloric Acid → 1-[(4-Bromo-2-fluorophenyl)methyl]-7-chloro-1H-indole-2,3-dione

HRID 1380293
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HRID 1380293 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[C:7]2=[O:12].C(=O)([O-])[O-].[K+].[K+].[Br:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[C:22]([F:28])[CH:21]=1.Cl>CN(C)C=O.ClC1C=CC=CC=1.O>[Br:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][N:9]2[C:10]3[C:6](=[CH:5][CH:4]=[CH:3][C:2]=3[Cl:1])[C:7](=[O:12])[C:8]2=[O:11])=[C:22]([F:28])[CH:21]=1
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참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 3441357-ChloroisatinHCID 27336604-Bromo-2-fluorobenzyl bromide

생성물 1

HCID 132480821-[(4-Bromo-2-fluorophenyl)methyl]-7-chloro-1H-indole-2,3-dione수율 50.9%

시약·촉매·용매 3

HCID 962Water
용매
HCID 6228Dimethylformamide용매
HCID 7964Chlorobenzene용매

실험 절차

A suspension of 7-chloro-indoline-2,3-dione (15 g.) and potassium carbonate (15 g.) in N,N-dimethylformamide (100 ml.) was stirred and treated with a solution of 4-bromo-2-fluorobenzyl bromide (24.7 g.) in chlorobenzene (100 ml.). The mixture was stirred at 90° C. for five hours; cooled to ambient temperature, and diluted with a mixture of water (500 ml.) and petrol 60-80 (500 ml.). The aqueous phase was adjusted to pH3 with 10M hydrochloric acid. The mixture obtained was separated by filtration. The solid obtained was washed with petrol 60-80, then with water, and recrystallised from ethanol to give 1-(4-bromo-2-fluorobenzyl)-7-chloro-indoline-2,3-dione (15.5 g.), m.p. 164°-166° C.

후처리

  1. stirringThe mixture was stirred at 90° C. for five hours
  2. customThe mixture obtained
  3. customwas separated by filtration
  4. customThe solid obtained
  5. washwas washed with petrol 60-80
  6. customwith water, and recrystallised from ethanol

출처 및 근거

ORD 기록
ord-214406e54a964139bbede9e5b80c44c5
출처 데이터셋
uspto-grants-1986_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04581366

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