Sodium Chloride → 4'-Methyl-2-nitro-1,1'-biphenyl

HRID 36206

반응식

HRID 36206 반응식
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([Sn](C)(C)C)=[CH:3][CH:2]=1.Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20].[OH-].[K+].[Na+].[Cl-]>[Cl-].[Cl-].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.[Pd+2].CCCCCC.CCOC(C)=O.CN(C=O)C>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])=[CH:3][CH:2]=1

참가 물질

8

반응물 4

HCID 5234Sodium ChlorideHCID 113411-Bromo-2-nitrobenzeneHCID 14797Potassium HydroxideHCID 617834Stannane, trimethyl(4-methylphenyl)-

생성물 1

HCID 104431944'-Methyl-2-nitro-1,1'-biphenyl수율 96.4%

시약·촉매·용매 3

HCID 84124Bis(triphenylphosphine)palladium chloride촉매HCID 6228Dimethylformamide용매HCID 21226206Ethyl acetate hexane용매

반응 조건

온도
110 °C

실험 절차

Under N2, a clean, dry flask was charged with p-tolyltrimethyltin (from Example 12, Step B) (5.61 g, 0.022 mol), 2-bromonitrobenzene (4.04 g, 0.020 mol), anhydrous DMF (40 mL), and palladium(II) bis(triphenylphosphine)dichloride (140 mg, 0.2 mmol), heated at 110° C. and stirred for 4 h when TLC (4:1 hexane/EtOAc) indicated disappearance of starting materials. The nearly black reaction mixture was cooled to room temperature, poured into a solution made from 100 mL 1N KOH and 100 mL sat. NaCl, and extracted with 3×150 mL EtOAc. The combined, organic layers were washed with 100 mL 1N KOH and 100 mL sat. NaCl, and then dried over anhydrous Na2SO4. After filtration, the amber solution was evaporated to dryness and then flash chromatographed over 900 mL SiO2, eluting with 2.5% EtOAc-hexane to give 4.109 g (96%) of the title compound as a light orange liquid, homogeneous on TLC (4/1 hex-EtOAc).

후처리

  1. customUnder N2, a clean, dry flask
  2. temperatureThe nearly black reaction mixture was cooled to room temperature
  3. additionpoured into a solution
  4. extractionextracted with 3×150 mL EtOAc
  5. washorganic layers were washed with 100 mL 1N KOH and 100 mL sat. NaCl
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationAfter filtration
  8. customthe amber solution was evaporated to dryness
  9. customflash chromatographed over 900 mL SiO2
  10. washeluting with 2.5% EtOAc-hexane

출처 및 근거

ORD 기록
ord-441fb8a42a0440f9bb92c91ede0b45b0
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05411980

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