Pyridine → 2-(2-Bromophenyl)pyridine

HRID 232087ノート

反応式

HRID 232087 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1N.N([O-])=O.[Na+].[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>Cl.O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 119922-BromoanilineHCID 23668193Sodium Nitrite

生成物 1

HCID 132239292-(2-Bromophenyl)pyridine

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒2 回

反応条件

温度
80 °C

実験手順

2-Bromobenzenamine (18.77 g) in 50 ml of conc HCl and 50 ml of water, was cooled in an ice bath and treated dropwise with stirring with a solution of sodium nitrite (8.28 g) in water (35 ml). After the addition was complete, the mixture was stirred in the ice bath for a further 30 minutes and then added portionwise (over 5 minutes) to pyridine (275 ml) stirred in an oil bath at 80° C. The mixture was heated (at 80° C.) for a further 1 hour, when the excess of pyridine was distilled off under reduced pressure. The residue was basified (aqueous sodium hydrogen carbonate) and extracted with ethyl acetate (3×). The extracts were washed with water (2×), dried (sodium sulphate) and evaporated to give a dark oil, which was flash chromatographed on silica using methylene chloride/ethyl acetate (20/1) as eluant. Pure sub-title compound (6.56 g) was obtained as a dark brown oil. m/z 235/233 (MW), 154 (Base Peak).

後処理

  1. additiontreated dropwise
  2. additionAfter the addition
  3. temperatureThe mixture was heated (at 80° C.) for a further 1 hour
  4. distillationwhen the excess of pyridine was distilled off under reduced pressure
  5. extractionextracted with ethyl acetate (3×)
  6. washThe extracts were washed with water (2×)
  7. dry with materialdried (sodium sulphate)
  8. customevaporated
  9. customto give a dark oil, which
  10. customchromatographed on silica
  11. customwas obtained as a dark brown oil

出典と根拠

ORDレコード
ord-28896b70318743ffa6606b617be365b3
出典データセット
uspto-grants-1989_07
特許番号
US04851419

反応ノート

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