Bromine → 4-(3-Bromo-4-methoxyphenyl)pyridine

HRID 1107287

反応式

HRID 1107287 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[Br:15]Br>C(O)(=O)C.O.[Fe]>[Br:15][C:8]1[CH:7]=[C:6]([C:9]2[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=2)[CH:5]=[CH:4][C:3]=1[O:2][CH3:1]

参加物

6

反応物 2

HCID 24408Bromine2 回HCID 6038134-(4-Methoxyphenyl)pyridine

生成物 1

HCID 184760964-(3-Bromo-4-methoxyphenyl)pyridine

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 176Acetic Acid溶媒3 回HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

4-(4-Methoxyphenyl)pyridine (1 g, 5.4 mmol) was dissolved in glacial acetic acid (6 ml). Iron powder (30 mg, 0.54 mmol) was added followed by a solution of bromine (0.36 ml) in glacial acetic acid (3 ml) slowly over 5 minutes. The resulting solution was stirred at 60° C. for 1 hour. A solution of bromine (0.13 ml) in glacial acetic acid (1 ml) was added and stirring was continued at 60° C. for 1.5 hours. The solution was allowed to cool to ambient temperature, diluted with water (20 ml). Excess bromine was destroyed by adding in sold sodium bisulphite until all the colour had disappeared. Solid sodium carbonate was added until the solution was basic and the resulting solution was then extracted with ethyl acetate (2×30 ml) and dried over sodium sulphate. Removal of the solvent gave an oil which was chromatographed on silica gel in diethyl ether giving the title compound as a clear oil (0.77 g, 54%). 1H NMR (250 MHz, CDCl3) δ 8.66-8.62 (2H, d, J=8.6 Hz), 7.87-7.86 (1H, d, J=2.2 Hz), 7.61-7.56 (1H, dd, J=8.5 Hz and 2.2 Hz), 7.48-7.46 (1H, d, J=8.5 Hz), 7.03-6.99 (2H, d, J=8.6 Hz), and 3.96 (3H, s). m/z (ES+) 264, 266 (M+1).

後処理

  1. stirringstirring
  2. waitwas continued at 60° C. for 1.5 hours
  3. temperatureto cool to ambient temperature
  4. customExcess bromine was destroyed
  5. additionby adding in sold sodium bisulphite until all the colour
  6. additionSolid sodium carbonate was added until the solution
  7. extractionthe resulting solution was then extracted with ethyl acetate (2×30 ml)
  8. dry with materialdried over sodium sulphate
  9. customRemoval of the solvent
  10. customgave an oil which
  11. customwas chromatographed on silica gel in diethyl ether giving the title compound as a clear oil (0.77 g, 54%)

出典と根拠

ORDレコード
ord-c0291c66fe7945558e0d4f5c91b4d080
出典データセット
uspto-grants-2000_05
特許番号
US06060469

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