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

HRID 1673189노트

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HRID 1673189 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 1140Toluene용매HCID 80711,2-Dimethoxyethane용매HCID 21867204Cyclohexane ethylacetate용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a785811753f444e9903adc4db75da154
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07999137B2

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