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

HRID 513313
ノート
印刷プレビュー

反応式

HRID 513313 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

HCID 866699709-(5-Bromo-2-nitrophenyl)phenanthrene収率 62%

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 962Water溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-89b570ea03e74f0f93bb467c4ebd9946
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09102616B2

反応ノート

読み込み中…

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