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Water → 4-[4-(4-Methoxyphenyl)phenoxy]-2,5-dimethylaniline

HRID 2070237
ノート
印刷プレビュー

反応式

HRID 2070237 の反応式
Br[C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[C:13]([CH3:14])=[CH:12][C:10]([NH2:11])=[C:9]([CH3:15])[CH:8]=2)=[CH:4][CH:3]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>C(O)CCC.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][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[CH:17]=[CH:16][C:5]([O:6][C:7]3[C:13]([CH3:14])=[CH:12][C:10]([NH2:11])=[C:9]([CH3:15])[CH:8]=3)=[CH:4][CH:3]=2)=[CH:22][CH:21]=1
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 962Water2 回HCID 10796Cesium carbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 685943334-(4-Bromophenoxy)-2,5-dimethylaniline

生成物 1

HCID 685954734-[4-(4-Methoxyphenyl)phenoxy]-2,5-dimethylaniline収率 79.7%

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 2631-Butanol溶媒

反応条件

温度
80 °C

実験手順

Under argon, 0.50 g (1.7 mmol) of 4-(4-bromophenoxy)-2,5-dimethylaniline and 0.34 g (2.2 mmol) of 4-methoxyphenylboronic acid are dissolved in 10 ml of 1-butanol and the solution is admixed with 2.23 g (6.8 mmol) of cesium carbonate, 39.5 mg (0.03 mmol) of tetrakis(triphenylphosphine)palladium(0) and 2.5 ml of water. The reaction mixture is stirred at 80° C. for 16 h, poured into water and extracted repeatedly with ethyl acetate. The combined organic phases are dried over Na2SO4 and filtered and the solvent is removed under reduced pressure. This is followed by purification by column chromatography (0.44 g, purity 99.0%, yield 79.7%, log P (pH 2.3)=3.06).

後処理

  1. extractionextracted repeatedly with ethyl acetate
  2. dry with materialThe combined organic phases are dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent is removed under reduced pressure
  5. customThis is followed by purification by column chromatography (0.44 g, purity 99.0%, yield 79.7%, log P (pH 2.3)=3.06)

出典と根拠

ORDレコード
ord-a224c70b0f8146909f206c83da8c33c5
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08299302B2

反応ノート

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