Sodium Carbonate → 2-(4'-Bromophenyl)aniline

HRID 746756

反応式

HRID 746756 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].I[C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH2:20]>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[NH2:20])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 119952-IodoanilineHCID 79599(4-Bromophenyl)boronic acid

生成物 1

HCID 113686332-(4'-Bromophenyl)aniline収率 69%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

Add 4-bromophenyl boronic acid (5.0 g, 24.82 mmol), tetrakis(triphenylphosphine) palladium (0) (0.717 g, 0.620 mmol) and 2 M Na2CO3 (10 mL) to a solution of 2-iodoaniline (4.5 g, 20.69 mmol) in toluene (2 mL):ethanol (20 mL), deoxygenate and heat at 80° C. under nitrogen. After 4 h, add water and extract with EtOAc. Combine the organic layers, dry over sodium sulfate, filter and concentrate under reduced pressure to give a residue. Purify the residue by flash chromatography (Silica gel-EtOAc/hexane 1:12), to provide 4′-bromo-biphenyl-2-ylamine (3.53 g, 69%). MS (m/e): 248 (M+1); 249 (M+2).

後処理

  1. customethanol (20 mL), deoxygenate
  2. additionadd water
  3. extractionextract with EtOAc
  4. dry with materialdry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. customto give a residue
  8. customPurify the residue by flash chromatography (Silica gel-EtOAc/hexane 1:12)

出典と根拠

ORDレコード
ord-00826bfc9c4b4b3895f2811d93cc2030
出典データセット
uspto-grants-2008_07
特許番号
US07393868B2

関連ノート

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