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

HRID 1384391

反応式

HRID 1384391 の反応式
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1>C(O)(=O)C>[Br:1][C:10]1[CH:9]=[C:8]([C:11]2[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=2)[CH:7]=[CH:6][C:5]=1[O:4][CH3:3]

参加物

4

反応物 2

HCID 24408BromineHCID 6038134-(4-Methoxyphenyl)pyridine

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
60 °C

実験手順

Bromine (26.0 g, 163 mmol) is added to a stirred solution of 4-(4-methoxyphenyl)pyridine (13.6 g. 73.5 mmol) in acetic acid (500 mL) and heated at 60° C. for 72 h. The mixture is then evaporated to dryness under reduced pressure and the residue is treated with aqueous ammonia (400 mL of 6M) and extracted with ethyl acetate (3×200 mL). The combined extracts are dried (Na2SO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by chromatography (silica gel, 95% t-butylmethyl ether/4.5% methanol/0.5% aqueous NH3(25%)) and recrystallised from ether-cyclohexane to give 4-(3-bromo-4-methoxyphenyl)pyridine as a pale-yellow crystalline solid, m.p. 82-84° C.

後処理

  1. customThe mixture is then evaporated to dryness under reduced pressure
  2. additionthe residue is treated with aqueous ammonia (400 mL of 6M)
  3. extractionextracted with ethyl acetate (3×200 mL)
  4. dry with materialThe combined extracts are dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent is evaporated off under reduced pressure
  7. customto yield the crude product which
  8. customis purified by chromatography (silica gel, 95% t-butylmethyl ether/4.5% methanol/0.5% aqueous NH3(25%))
  9. customrecrystallised from ether-cyclohexane

出典と根拠

ORDレコード
ord-95e315002c0145a79be5406ed4f4b68b
出典データセット
uspto-grants-2001_07
特許番号
US06258843B1

関連ノート

読み込み中…