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

HRID 31305

Reaction equation

HRID 31305 reaction equation
[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

Participants

3

Reactant 2

HCID 90073-MethoxyphenolHCID 676173-Fluorophenylacetic acid

Product 1

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

Conditions

Temperature
65 °C

Procedure

(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).

Workup

  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

Sources & evidence

ORD record
ord-1391c4fde4464f7eb0e82249779eb5ee
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Linked notes

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