Toluene → 2-(4'-Bromophenyl)aniline

HRID 746762

반응식

HRID 746762 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 113686332-(4'-Bromophenyl)aniline수율 64%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-637d8c2b089c435c9e47f43bbec47e09
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07393868B2

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