Water → 4'-Tert-butyl-2,5-dimethylbiphenyl-4-amine

HRID 1673189ノート

反応式

HRID 1673189 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:15]1[C:21]([CH3:22])=[CH:20][C:18]([NH2:19])=[C:17]([CH3:23])[CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>COCCOC.C1CCCCC1.C(OC(=O)C)C.C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:15]2[CH:16]=[C:17]([CH3:23])[C:18]([NH2:19])=[CH:20][C:21]=2[CH3:22])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

8

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27343204-tert-Butylphenylboronic acidHCID 81671304-Bromo-2,5-dimethylaniline

生成物 1

HCID 598436854'-Tert-butyl-2,5-dimethylbiphenyl-4-amine収率 72.3%

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 21867204Cyclohexane ethylacetate溶媒

反応条件

温度
80 °C

実験手順

The reaction is carried out using inert conditions (argon or nitrogen atmosphere, dry solvents). A suspension of 6.4 g (36.0 mmol) of (4-tert-butylphenyl)boronic acid, 6.0 g (30.0 mmol) of 4-bromo-2,5-dimethylaniline, 29.3 g (90 mmol) caesium carbonate and 0.7 g (0.6 mmol) tetrakis(triphenylphosphin)palladium in 75 ml of 1,2-dimethoxyethan was stirred for 16 hrs at 80° C. At room temperature 25 ml of water and 75 ml of toluene were added. The organic layer was separated, the watery layer was again extracted using 75 ml of toluene. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. Column chromatographic (cyclohexane/ethylacetate:2/1) yielded 5.5 g (21.7 mmol) 72% of 4′-tert-butyl-2,5-dimethylbiphenyl-4-amine (log P (pH 2.3)=3.65.

後処理

  1. customThe organic layer was separated
  2. extractionthe watery layer was again extracted
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a785811753f444e9903adc4db75da154
出典データセット
uspto-grants-2011_08
特許番号
US07999137B2

反応ノート

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