3-(1,1-DIFLUOROETHYL)BENZOIC ACID synthesis
- Product Name:3-(1,1-DIFLUOROETHYL)BENZOIC ACID
- CAS Number:55805-17-9
- Molecular formula:C9H8F2O2
- Molecular Weight:186.16
878745-29-0
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55805-17-9
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Yield:55805-17-9 68%
Reaction Conditions:
with lithium hydroxide in methanol at 20; for 16 h;
Steps:
4
In a plastic reaction vessel equipped with a Teflon-coated magnetic stiffer was charged DEOXO-FLUOR (6 eq., 2.7 M solution in toluene). To this was then added sequentially 3-acetyl-benzoic acid methyl ester (1 eq.) and ethanol (1 eq.), and the resulting mixture was heated at 85°C for 3 days. The reaction mixture was then cooled to RT, diluted with EtOAc and washed with brine. The organic extract was then dried over MgSO4, filtered and the filtrate concentrated in vacuo. Purification of the residue thus obtained by way of column chromatography (Si02, gradient elution, Hex -> 9:1 (v/v) Hex: EtOAc) afforded the intermediate ester as a colorless oil. This was then immediately taken up in methanol (0.1 M), added lithium hydroxide (1 eq.) and then stirred at RT for 16 h. The resulting reaction mixture was carefully neutralized with HC1 (4 M in dioxane) and the volatiles were removed in vacuo. The resulting residue was subjected to column chromatography (Si02, gradient elution, 9:1 (v/v) Hex: EtOAc-> EtOAc) to furnish the desired product as a white solid (68% yield).
References:
WO2017/49068,2017,A1 Location in patent:Paragraph 00172
55805-06-6
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6136-68-1
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21860-07-1
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55805-17-9
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2142-63-4
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55805-17-9
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