4-Bromo-2-nitroaniline → 2'-Fluoro-3-nitro-[1,1'-biphenyl]-4-amine

HRID 1518142ノート

反応式

HRID 1518142 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O.C([O-])(O)=O.[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>[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

参加物

7

反応物 3

HCID 701324-Bromo-2-nitroanilineHCID 516892Sodium BicarbonateHCID 27343542-Fluorophenylboronic acid

生成物 1

HCID 224778582'-Fluoro-3-nitro-[1,1'-biphenyl]-4-amine収率 78%

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 solution of 4-bromo-2-nitro-phenylamine (2.17 g, 10.0 mmol) in dioxane (40 mL) was treated with 2-fluorophenylboronic acid (1.40 g, 10.0 mmol) and NaHCO3 (40.0 mL, 80.0 mmol, 2M aqueous). The mixture was degassed via sonication and flushed with Ar. Pd(PPh3)4 (116 mg, 0.100 mmol) was added, and the mixture was heated to 80° C. for 12 h. The mixture was diluted with water (40 mL) and extracted twice with EtOAc (40 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo. The residue was purified on silica (EtOAc/hexanes, 0:1 to 1:1, v/v) to obtain 1.80 g (78%) of the title compound. 1H-NMR (400 MHz, CDCl3) δ: 8.36 (d, J=1.8 Hz, 1H), 7.64 (dt, J=8.6, 2.0 Hz, 1H), 7.45 (td, J=7.8, 1.8 Hz, 1H), 7.30-7.38 (m, 1H), 7.13-7.27 (m, 2H), 6.91 (d, J=8.6 Hz, 1H), 6.18 (br. s., 2H).

後処理

  1. customThe mixture was degassed via sonication
  2. customflushed with Ar
  3. extractionextracted twice with EtOAc (40 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on silica (EtOAc/hexanes, 0:1 to 1:1

出典と根拠

ORDレコード
ord-8e13399615f143f28a896fea6299fbf6
出典データセット
uspto-grants-2012_07
特許番号
US08232409B2

反応ノート

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