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Toluene → HCID 59489285、化合物

HRID 385309
ノート
印刷プレビュー

反応式

HRID 385309 の反応式
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:30]=[CH:29][C:28]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15]=3[CH:14]=2)[CH:8]=1)(=O)=O.[CH3:33][O:34][C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][CH:40]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.O>[CH3:33][O:34][C:35]1[CH:36]=[C:37]([C:11]2[CH:12]=[CH:7][CH:8]=[C:9]([C:13]3[CH:30]=[CH:29][C:28]4[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[C:15]=4[CH:14]=3)[CH:10]=2)[CH:38]=[CH:39][CH:40]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 2734370(3-Methoxyphenyl)boronic acidHCID 592458333-(Triphenylen-2-yl)phenyl trifluoromethanesulfonate

生成物 1

HCID 59489285HCID 59489285、化合物収率 98.2%

試薬・触媒・溶媒 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl触媒
HCID 962Water溶媒

実験手順

12.9 g (28.5 mmol) 3-(triphenylen-2-yl)phenyl trifluoromethanesulfonate, 6.5 g (42.8 mmol) 3-methoxyphenylboronic acid, 0.47 g (1.1 mmol) 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos) and 18.2 g (85.5 mmol) potassium phosphate tribasic (K3PO4) were weighed in a round bottom flask. 150 mL toluene and 80 mL water were added to the flask as solvent. The solution was purged with nitrogen and 0.26 g (0.28 mmol) of tris(dibenzylideneacetone)dipalladium (0) [Pd2(dba)3] was added. The solution was heated to reflux for twelve hours. Upon cooling, the organic layer was separated, and dried with MgSO4. The product was readily separated by column chromatography using hexane/dichloromethane as eluent (1/0 gradient to 3/2). The solvent was removed by rotary evaporation resulting in 11.7 g (28 mmol) of the product, 2-(3′-methoxybiphenyl-3-yl)triphonylene.

後処理

  1. additionwas added
  2. temperatureThe solution was heated
  3. temperatureto reflux for twelve hours
  4. temperatureUpon cooling
  5. customthe organic layer was separated
  6. dry with materialdried with MgSO4
  7. customThe product was readily separated by column chromatography
  8. customThe solvent was removed by rotary evaporation

出典と根拠

ORDレコード
ord-543217797b774adf9fa7e0b7986b10ff
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08367850B2

反応ノート

読み込み中…

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