Toluene → (2-(2,2,2-Trifluoroethoxy)-phenyl)-aniline

HRID 2053054ノート

反応式

HRID 2053054 の反応式
[F:1][C:2]([F:13])([F:12])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1Br.C1(C)C=CC=CC=1.[NH2:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.C(O)C>[F:1][C:2]([F:13])([F:12])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

参加物

7

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 922693-Aminophenylboronic acidHCID 226154791-Bromo-2-(2,2,2-trifluoroethoxy)benzene

生成物 1

HCID 20080993(2-(2,2,2-Trifluoroethoxy)-phenyl)-aniline

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒

反応条件

温度
90 °C

実験手順

To a solution of 1.0 g (3.93 mmol) of 2-trifluoroethoxyphenyl bromide (Example 3, Step A) in 39 Ml of toluene was added 0.136 g (0.118 mmol) of tetrakis(triphenylphosphine)palladium(0), 0.56 g (4.31 mol) of 3-aminophenylboronic acid, 47 Ml (94.1 mmol) of a 2M solution of sodium carbonate and 8 Ml of ethanol and the reaction mixture was heated at 90° C. for 22 hr. The reaction mixture was cooled to RT, and partitioned between water and EtOAc. The aqueous fraction was extracted with EtOAc and the combined organic fractions were washed with water and brine and dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, 4:1 hexanes:EtOAc) to give the title compound. Mass Spectrum (ESI) m/e M+1 268.1.

後処理

  1. temperatureThe reaction mixture was cooled to RT
  2. custompartitioned between water and EtOAc
  3. extractionThe aqueous fraction was extracted with EtOAc
  4. washthe combined organic fractions were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by chromatography (silica, 4:1 hexanes:EtOAc)

出典と根拠

ORDレコード
ord-95403d0c2e6445d69854a4e0ab9e14e6
出典データセット
uspto-grants-2008_02
特許番号
US07326726B2

反応ノート

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