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

HRID 746756

반응식

HRID 746756 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 113686332-(4'-Bromophenyl)aniline수율 69%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-00826bfc9c4b4b3895f2811d93cc2030
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07393868B2

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