Sodium Carbonate → 4'-Chloro-2'-methyl-[1,1'-biphenyl]-4-amine

HRID 1401880ノート

反応式

HRID 1401880 の反応式
I[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH3:9][C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCO.O>[Cl:16][C:14]1[CH:13]=[CH:12][C:11]([C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=2)=[C:10]([CH3:9])[CH:15]=1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 108934-IodoanilineHCID 5017600(4-Chloro-2-methylphenyl)boronic acid

生成物 1

HCID 672116234'-Chloro-2'-methyl-[1,1'-biphenyl]-4-amine

試薬・触媒・溶媒 1

HCID 86587095Dimethoxyethane ethanol water溶媒

反応条件

温度
125 °C

実験手順

A mixture of 4-iodo-aniline (25.0 g, 114.1 mmol), 2-methyl-4-chlorophenyl-boronic acid (29.17 g, 171.1 mmol), PdCl2(P(o-tolyl)3)2 (11.66 g, 14.8 mmol), and Na2CO3 (60.49 g, 570.7 mmol) in DME/EtOH/H2O (100/50/25 mL) was heated 125° C. for 2 h. The reaction mixture was cooled to room temperature, filtered and washed with EtOAc (200 mL). The solvent was removed under reduced pressure. The crude mixture was extracted with ethyl acetate (500 mL) and the organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The resulting crude was purified by column chromatography on silica gel, eluting with 5-30% Hexane/EtOAc to afford 4′-Chloro-2′-methyl biphenyl-4-ylamine. 1H NMR (300 MHz, CDCl3): δ 7.24-7.08 (m, 5 H), 6.72 (d. J=7.2 Hz, 2 H), 3.70 (bs, 2 H), 2.27 (s, 3 H).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. washwashed with EtOAc (200 mL)
  4. customThe solvent was removed under reduced pressure
  5. extractionThe crude mixture was extracted with ethyl acetate (500 mL)
  6. washthe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting crude was purified by column chromatography on silica gel
  10. washeluting with 5-30% Hexane/EtOAc

出典と根拠

ORDレコード
ord-a6ab28a8dce341ad8d9760561ccdfb65
出典データセット
uspto-grants-2014_12
特許番号
US08907103B2

反応ノート

読み込み中…