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

HRID 405001
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HRID 405001 반응식
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
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7

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HCID 962Water2회HCID 10796Cesium carbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 685943334-(4-Bromophenoxy)-2,5-dimethylaniline

생성물 1

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

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 2631-Butanol용매

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온도
80 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-4217c8e5fae54f409027707d6f0b7123
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08748662B2

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