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

HRID 628213

反応式

HRID 628213 の反応式
[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

参加物

6

反応物 3

HCID 68292-NitrobiphenylHCID 24408BromineHCID 516919Sodium Bisulfate

生成物 1

HCID 218576474'-Bromo-2-nitrobiphenyl収率 35%

試薬・触媒・溶媒 2

HCID 24380Iron chloride (FeCl3)触媒HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c9cc7bbbc0a64954932224745e35b818
出典データセット
uspto-grants-2016_04
特許番号
US09312502B2

関連ノート

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