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Tetrahydrofuran → 9-(5-Bromo-2-nitrophenyl)phenanthrene

HRID 513313
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HRID 513313 반응식
B(O)(O)[C:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.C1COCC1.Br[C:24]1[CH:29]=[C:28]([Br:30])[CH:27]=[CH:26][C:25]=1[N+:31]([O-:33])=[O:32].[OH-].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[Br:30][C:28]1[CH:27]=[CH:26][C:25]([N+:31]([O-:33])=[O:32])=[C:24]([C:2]2[C:15]3[C:10]([C:9]4[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=4[CH:3]=2)=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:29]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 117757049-Phenanthracenylboronic acidHCID 123156462,4-Dibromo-1-nitrobenzene

생성물 1

HCID 866699709-(5-Bromo-2-nitrophenyl)phenanthrene수율 62%

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 962Water용매

실험 절차

A 2 L round bottom flask was charged with phenanthracene-9-boronic acid (76.61 g, 345 mmol), THF (700 mL), and H2O (350 mL), and the mixture was dissolved. To the resultant mixture, 2,4-dibromo-1-nitrobenzene (146 g, 518 mmol), NaOH (42 g, 1035 mmol), and Pd(PPh3)4 (20 g, 17.3 mmol) were sequentially added, followed by reaction at 80° C. for 24 hours. After the reaction was completed, the resultant product was extracted with methylene chloride, water, and brine, and the organic layer was dried with MgSO4. The obtained organic layer was purified by silica gel column (methylene chloride:hexane=1:3) so as to give 80.4 g of a product (62%).

후처리

  1. dissolutionthe mixture was dissolved
  2. customfollowed by reaction at 80° C. for 24 hours
  3. extractionthe resultant product was extracted with methylene chloride, water, and brine
  4. dry with materialthe organic layer was dried with MgSO4
  5. customThe obtained organic layer was purified by silica gel column (methylene chloride:hexane=1:3) so as

출처 및 근거

ORD 기록
ord-89b570ea03e74f0f93bb467c4ebd9946
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09102616B2

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