Toluene → 2-(4'-Bromophenyl)aniline

HRID 746762

反応式

HRID 746762 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.I[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18].C1(C)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 119952-IodoanilineHCID 79599(4-Bromophenyl)boronic acid

生成物 1

HCID 113686332-(4'-Bromophenyl)aniline収率 64%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

Combine 4-bromophenylboronic acid (6.064 g, 30.195 mmol), 2-iodo-phenylamine (5.532 g, 25.257 mmol), toluene, 2N Na2CO3 (13 ml, 26 mmol), and tetrakis(triphenyl-phosphine)palladium(0) (0.849 g) and heat to 80° C. After 4 hours cool to room temperature and stir for 16 hours. Dilute the reaction with EtOAc and back extract water layer with EtOAc. Combine the organic layers and wash with H2O, and dry over Na2SO4, filter, and concentrate under reduced pressure. Purify the residue by flash chromatography (silica gel), eluting with first hexane and increasing up to 10% EtOAc/Hexane to afford 4′-bromo-biphenyl-2-ylamine (4.008 g, 64%). LCMS 247.

後処理

  1. additionDilute
  2. washwash with H2O
  3. dry with materialdry over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. customPurify the residue by flash chromatography (silica gel)
  7. washeluting with first hexane
  8. temperatureincreasing up to 10% EtOAc/Hexane

出典と根拠

ORDレコード
ord-637d8c2b089c435c9e47f43bbec47e09
出典データセット
uspto-grants-2008_07
特許番号
US07393868B2

関連ノート

読み込み中…