Methanone, (5-fluoro-2-hydroxyphenyl)phenyl- synthesis

9synthesis methods

Product Name:Methanone, (5-fluoro-2-hydroxyphenyl)phenyl-
CAS Number:362-47-0
Molecular formula:C13H9FO2
Molecular Weight:216.2078

Preparation by demethylation of 5-fluoro-2-methoxybenzophenone with refluxing pyridinium chloride.

591-50-4 Synthesis

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347-54-6
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Methanone, (5-fluoro-2-hydroxyphenyl)phenyl-

362-47-0
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Yield:362-47-0 64.2%

Reaction Conditions:

with sodium hydrogencarbonate;lithium chloride;palladium dichloride in N,N-dimethyl-formamide at 110;Inert atmosphere;

Steps:

(3,4-difluorophenyl)(2-hydroxy-4-methoxyphenyl)methanone

General procedure: A vial was charged with 2-Hydroxy-4-methoxybenzaldehyde (1.97 mmol, 300 mg), PdCl₂ (5 mol%, 17.5 mg), 1,2-Difluoro-4-iodobenzene (2 equiv., 946.7 mg), Na₂CO₃ (2 equiv., 418.1 mg), LiCl (0.4 equiv., 16.7 mg), and DMF (19.7 mL, 0.1 M of the aldehyde), purged with N₂ and stirred at 110 °C 4-10 h. The reaction was monitored with LC-MS and TLC (TLC conditions: Aliquot was diluted with CH₃OH, eluted with EtOAc/heptane 1:3, and stained with 2,4- dinitrophenylhydrazine solution). The reaction mixture was filtered over a pad of Celite, diluted with EtOAc, washed 3 times with water, and the aqueous layers was acidified and extracted twice with EtOAc. The combined organic layers was dried over Na₂SO₄, concentrated and purified on silica using EtOAc/Heptane 1:20 → 1:9 step gradient) to afford 2'-hydroxybenzophenone in 69.3% yield. (NMR data is given in the supporting information).

References:

Saleeb, Michael;Mojica, Sergio;Eriksson, Anna U.;Andersson, C. David;Gylfe, ?sa;Elofsson, Mikael [European Journal of Medicinal Chemistry,2018,vol. 143,p. 1077 - 1089] Location in patent:supporting information

371-41-5 Synthesis