Preparation of organic compounds bearing a trifluoromethyl group on a quaternary carbon
OwnerGauri Sankar Lal, Michael Ulman +1inventors
InventorsGauri Sankar Lal, Michael Ulman, William Jack Casteel
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Abstract
A method for preparing a molecule bearing a trifluoromethyl group on a quaternary carbon atom, includes providing a reactant having a quaternary carbon atom bearing a carboxylic acid group and an electron withdrawing group; and reacting the reactant with SF4 in a solvent to substitute the carboxylic acid group with the trifluoromethyl group and provide a reaction product mixture including the molecule bearing the trifluoromethyl group on the quaternary carbon atom.
Claims17
A method for preparing a molecule bearing a trifluoromethyl group on a quaternary carbon atom, said method comprising:
- providing a reactant comprising a quaternary carbon atom bearing a carboxylic acid group and an electron withdrawing group;
- and
- reacting the reactant with SF4 in a solvent to substitute the carboxylic acid group with the trifluoromethyl group and provide a reaction product mixture comprising the molecule bearing the trifluoromethyl group on the quaternary carbon atom.
A method for preparing a molecule bearing a trifluoromethyl group and an alkyl group on a quaternary carbon atom, said method comprising the sequential steps of:
- providing a reactant comprising a quaternary carbon atom bearing a carboxylic acid group and an ester group;
- reacting the reactant with SF4 in a solvent to substitute the carboxylic acid group with the trifluoromethyl group;
- and substituting the alkyl group for the ester group to provide the molecule bearing the trifluoromethyl group and the alkyl group on the quaternary carbon atom
A method for preparing a molecule bearing a trifluoromethyl group on a quaternary carbon atom, said method represented by the following equation:
- where:
- (i) R1 is an electron withdrawing group selected from the group consisting of:
- (a) carboxylic acid esters, COOR′, where R′ is unsubstituted alkyl, substituted alkyl, unsubstituted aryl, or substituted aryl of 1-20 carbon atoms;
- (b) NO2;
- (c) SOR, where R is alkyl or aryl;
- (d) SO2R, where R is alkyl or aryl;
- (e) POOR3, where R is alkyl or aryl;
- (f) PR3, where R is alkyl or aryl;
- and (g) CN, and
- (ii) R3, R4 is cycloalkyl of 3-8 carbon atoms, or
- (iii) R3 and R4 are independently selected from the group consisting of unsubstituted alkyl, substituted alkyl, unsubstituted aryl, and substituted aryl of 1-20 carbon atoms.
Dependencies are inferred from the claim text.