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Potassium Carbonate → 1-(3-Methyl-4'-trifluoromethyl-biphenyl-4-yl)-ethanone

HRID 1669224
ノート
印刷プレビュー

反応式

HRID 1669224 の反応式
[C:1]([C:4]1[CH:9]=[CH:8][C:7](OS(C(F)(F)F)(=O)=O)=[CH:6][C:5]=1[CH3:18])(=[O:3])[CH3:2].[F:19][C:20]([F:31])([F:30])[C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O.CCCCCC>O1CCOCC1.O.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>[CH3:18][C:5]1[CH:6]=[C:7]([C:24]2[CH:25]=[CH:26][C:21]([C:20]([F:31])([F:30])[F:19])=[CH:22][CH:23]=2)[CH:8]=[CH:9][C:4]=1[C:1](=[O:3])[CH3:2]
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

7

反応物 4

HCID 11430Potassium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 114829354-Acetyl-3-methylphenyl trifluoromethanesulfonateHCID 21226206Ethyl acetate hexane

生成物 1

HCID 673427591-(3-Methyl-4'-trifluoromethyl-biphenyl-4-yl)-ethanone収率 96%

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 218864351,4-Dioxane--water (1/1)溶媒

反応条件

温度
80 °C

実験手順

To an ambient temperature solution of trifluoro-methanesulfonic acid 4-acetyl-3-methyl-phenyl ester (6.10 g, 21.61 mmol) in dioxane/water (150/30 mL) is added 4-(trifluoromethyl)phenylboronic acid (4.51 g, 23.77 mmol), potassium carbonate (4.48 g, 32.42 mmol) and the reaction mixture is degassed with nitrogen for 20 min. Tetrakis(triphenylphosphine)palladium (1.25 g, 1.08 mmol) is added and the reaction mixture is heated to 80° C. overnight. TLC (10% EtOAc/hexane) indicates complete consumption of starting material. The reaction mixture is concentrated and chromatographed (330 g SiO2, 5% EtOAc/Hexanes) to yield the title compound (5.77 g, 96%). 1NMR (400 MHz, CDCl3) δ ppm: 7.82 (d, 1H, J=7.9 Hz), 7.72 (s, 4H), 7.51-7.46 (m, 2H), 2.63 (s, 3H), 2.62 (s, 3H).

後処理

  1. customthe reaction mixture is degassed with nitrogen for 20 min
  2. customconsumption of starting material
  3. concentrationThe reaction mixture is concentrated
  4. customchromatographed (330 g SiO2, 5% EtOAc/Hexanes)

出典と根拠

ORDレコード
ord-054080ad3a9c4cc4aee96800ee2270fb
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07989457B2

反応ノート

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