4-Bromo-2-methylaniline → 4'-Chloro-3-methylbiphen-4-ylamine

HRID 72294

反応式

HRID 72294 の反応式
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.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:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:3]=[C:4]([CH3:9])[C:5]([NH2:6])=[CH:7][CH:8]=2)=[CH:13][CH:12]=1

参加物

7

反応物 3

HCID 114234-Bromo-2-methylanilineHCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acid

生成物 1

HCID 230051884'-Chloro-3-methylbiphen-4-ylamine収率 70.8%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

To a stirred, degassed solution of 4-bromo-2-methylaniline (20 g, 0.107 mol) in toluene (1200 ml) and ethanol (400 ml), under an atmosphere of nitrogen, is added 4-chlorophenylboronic acid (20.32 g, 0.13 mol) and the reaction mixture is stirred and heated to 80° C. Tetrakis(triphenylphosphine)palladium(0) (2.48 g, 0.002 mol) is added to the reaction mixture, and to this is added 2M aqueous potassium carbonate solution (160 ml). The reaction mixture is heated at reflux for 4 hours, then cooled to room temperature. The reaction mixture was filtered through diatomaceous earth, and the filtrate was evaporated under reduced pressure. The residue is partitioned between ethyl acetate and water. The aqueous phase is extracted with ethyl acetate (3×500 ml) and the organic extracts are combined and concentrated under reduced pressure to give 4′-chloro-3-methylbiphen-4-ylamine (16.5 g).

後処理

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 4 hours
  3. temperaturecooled to room temperature
  4. filtrationThe reaction mixture was filtered through diatomaceous earth
  5. customthe filtrate was evaporated under reduced pressure
  6. customThe residue is partitioned between ethyl acetate and water
  7. extractionThe aqueous phase is extracted with ethyl acetate (3×500 ml)
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-0b68e4c523be4516942519bf2ea1b464
出典データセット
uspto-grants-2014_09
特許番号
US08828908B2

関連ノート

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