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

HRID 1384391

반응식

HRID 1384391 반응식
[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]

참가 물질

4

반응물 2

HCID 24408BromineHCID 6038134-(4-Methoxyphenyl)pyridine

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-95e315002c0145a79be5406ed4f4b68b
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06258843B1

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