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Cesium fluoride → 1-{[2,4-bis(methyloxy)phenyl]methyl}-3-methyl-4-[4-(trifluoromethyl)phenyl]-1H-pyrrole-2,5-dione

HRID 1513336
ノート
印刷プレビュー

反応式

HRID 1513336 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][N:12]1[C:16](=[O:17])[C:15]([CH3:18])=[C:14](Br)[C:13]1=[O:20].[F:21][C:22]([F:33])([F:32])[C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.[F-].[Cs+]>[Cl-].C([N+](CC)(CC1C=CC=CC=1)CC)C.C1(C)C=CC=CC=1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][N:12]1[C:13](=[O:20])[C:14]([C:26]2[CH:27]=[CH:28][C:23]([C:22]([F:33])([F:32])[F:21])=[CH:24][CH:25]=2)=[C:15]([CH3:18])[C:16]1=[O:17]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 3

HCID 25953Cesium fluorideHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 12013927{[2,4-bis(methyloxy)phenyl]methyl}-3-bromo-4-methyl-1H-pyrrole-2,5-dione

生成物 1

HCID 594961041-{[2,4-bis(methyloxy)phenyl]methyl}-3-methyl-4-[4-(trifluoromethyl)phenyl]-1H-pyrrole-2,5-dione収率 115.7%

試薬・触媒・溶媒 4

HCID 66133
Benzyl triethylammonium chloride
触媒
HCID 178418476HCID 178418476、化合物触媒
HCID 962Water溶媒
HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

{[2,4-bis(methyloxy)phenyl]methyl}-3-bromo-4-methyl-1H-pyrrole-2,5-dione (P9, 3.3, 9.7 mmol), [4-(trifluoromethyl)phenyl]boronic acid (3.68 g, 19.40 mmol), bis(triphenylphosphine)palladium(ii) chloride (0.601 g, 0.91 mmol) and cesium fluoride (3.98 g, 26.2 mmol) and N,N-diethyl-N-(phenylmethyl)ethanaminium chloride (0.22 g, 0.970 mmol) were dissolved in Toluene (60 mL)/Water (60.0 mL) and the reaction mixture was stirred at 90° C. overnight. Toluene was evaporated under reduced pressure and a saturated solution of NH4Cl was added. The aqueous phase was extracted with DCM, solvent was eliminated under reduced pressure and crude product by flash chromatography (Biotage SiO2, eluent: Cy/AcOEt 98:2; fraction volume: 45 mL) affording 1-{[2,4-bis(methyloxy)phenyl]methyl}-3-methyl-4-[4-(trifluoromethyl)phenyl]-1H-pyrrole-2,5-dione (P10, 4.55 g, 11.22 mmol)

後処理

  1. customToluene was evaporated under reduced pressure
  2. additiona saturated solution of NH4Cl was added
  3. extractionThe aqueous phase was extracted with DCM, solvent

出典と根拠

ORDレコード
ord-ab6cb544f80e496a894af18528d2791b
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08217168B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート