3-Methoxyphenol → 2-(3-Fluorophenyl)-1-(2-hydroxy-4-methoxyphenyl)ethanone

HRID 31305

반응식

HRID 31305 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=1>>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([C:17]2[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][C:16]=2[OH:20])=[O:11])[CH:5]=[CH:6][CH:7]=1

참가 물질

3

반응물 2

HCID 90073-MethoxyphenolHCID 676173-Fluorophenylacetic acid

생성물 1

HCID 179785042-(3-Fluorophenyl)-1-(2-hydroxy-4-methoxyphenyl)ethanone

반응 조건

온도
65 °C

실험 절차

(3-Fluorophenyl)acetic acid (3.7 g) and 3-methoxyphenol (3.0 g) were dissolved into BF3Et2O (60 ml, 20 eq) under argon. The mixture was stirred at 60-70° C. until disappearance of the starting materials (9 h) and poured into large volume of ice water. After extraction with ethyl acetate the combined organic layers were washed with water, dried and evaporated. The crude product was purified by column chromatography using CH2Cl2 as an eluant. 1H NMR (400 MHz, d6-DMSO) δ: 12.41 (br s, 1H), 8.02 (d, 1H, J 9.0 Hz), 7.34-7.38 (m, 1H), 7.09-7.13 (m, 3H), 6.56 (dd, 1H, J 9.0, 2.5 Hz), 6.49 (d, 1H, J 2.5 Hz), 4.41 (s, 2H), 3.83 (s, 3H).

후처리

  1. extractionAfter extraction with ethyl acetate the combined organic layers
  2. washwere washed with water
  3. customdried
  4. customevaporated
  5. customThe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-1391c4fde4464f7eb0e82249779eb5ee
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425568B2

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