2-Nitrobiphenyl → 4'-Bromo-2-nitrobiphenyl

HRID 628213

반응식

HRID 628213 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([O-:3])=[O:2].[Br:16]Br.S(=O)(=O)(O)[O-].[Na+]>[Fe](Cl)(Cl)Cl.O>[Br:16][C:13]1[CH:12]=[CH:11][C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])=[CH:15][CH:14]=1

참가 물질

6

반응물 3

HCID 68292-NitrobiphenylHCID 24408BromineHCID 516919Sodium Bisulfate

생성물 1

HCID 218576474'-Bromo-2-nitrobiphenyl수율 35%

시약·촉매·용매 2

HCID 24380Iron chloride (FeCl3)촉매HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

A three neck flask was charged with 2-nitrobiphenyl (1 mol), iron trichloride (55 mmol), and water (200 mL) and set to stir under a nitrogen atmosphere for 30 minutes. Bromine (1.25 mol) was added dropwise over the course of one hour, then set to reflux for four hours, cooled to 60° C., and stirred for 12 hours. Sodium bisulfate (500 mmol) was added slowly, and the mixture rinsed three times with water (200 mL), twice with 5% sodium hydroxide solution (100 ml) and twice more with water (200 mL). The solids were dissolved in dichloromethane, dried over magnesium sulfate, and flashed chromatographed over silica with dichloromethane as the eluent. The solvent was removed under reduced pressure and the crude product recrystallized from ethanol to give 4′-bromo-2-nitrobiphenyl in 35% yield.

후처리

  1. temperatureto reflux for four hours
  2. stirringstirred for 12 hours
  3. washthe mixture rinsed three times with water (200 mL)
  4. dissolutionThe solids were dissolved in dichloromethane
  5. dry with materialdried over magnesium sulfate
  6. customflashed chromatographed over silica with dichloromethane as the eluent
  7. customThe solvent was removed under reduced pressure
  8. customthe crude product recrystallized from ethanol

출처 및 근거

ORD 기록
ord-c9cc7bbbc0a64954932224745e35b818
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09312502B2

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