Boron trifluoride etherate → 2-(3-Fluorophenyl)-1-(2-hydroxy-4-methoxyphenyl)ethanone

HRID 1455028Notes

Reaction equation

HRID 1455028 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.B(F)(F)F.CCOCC>>[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

4

Reactant 3

HCID 8000Boron trifluoride etherateHCID 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 BF3.Et2O (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-259457dcd2d7481eb605a3fa84a1467b
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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