Sodium Carbonate → 2',5',6-Trichloro-4-methoxy-[1,1'-biphenyl]-3-amine

HRID 588814

反応式

HRID 588814 の反応式
[Cl:1][C:2]1[C:7](I)=[CH:6][C:5]([NH2:9])=[C:4]([O:10][CH3:11])[CH:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.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>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[C:7]1[C:2]([Cl:1])=[CH:3][C:4]([O:10][CH3:11])=[C:5]([NH2:9])[CH:6]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 27733712,5-Dichlorobenzeneboronic acidHCID 917583774-Chloro-5-iodo-2-methoxyaniline

生成物 1

HCID 904558872',5',6-Trichloro-4-methoxy-[1,1'-biphenyl]-3-amine収率 75.8%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

A mixture of 4-chloro-5-iodo-2-methoxybenzenamine (4.1 g, 14.5 mmol), 2,5-dichlorophenylboronic acid (3.3 g, 17.4 mmol), Pd(PPh3)4 (500 mg, 1.45 mmol) and Na2CO3 (4.7 g, 43.5 mmol) in 1,4-dioxane (150 mL) and water (15 mL) was stirred at 80° C. under argon for 16 h. The mixture was allowed to cool to room temperature, and then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=20:1) to afford the desired product (3.3 g, 75.8% yield) as an off-white solid.

後処理

  1. temperatureto cool to room temperature
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=20:1)

出典と根拠

ORDレコード
ord-17ba0b5f9ac646d1aa09009a88c295b6
出典データセット
uspto-grants-2016_01
特許番号
US09227978B2

関連ノート

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