Intermediates and processes for preparing substituted chromanol derivatives

A process of preparing a compound having formula IX,

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• or the enantiomer of said compound, wherein R1 is —(CH2)qCHR5R6 and q is 0 to 4;
• each R2 and R3 is independently selected from the group consisting of H, fluoro, chloro, C1-C6 alkyl, C1-C6 alkoxy, phenylsulfinyl, phenylsulfonyl, and —S(O)n(C1-C6 alkyl) where n is 0 to 2, and said alkyl group, the alkyl moiety of said alkoxy and —S(O)n(C1-C6 alkyl) groups, and the phenyl moiety of said phenylsulfinyl and phenylsulfonyl groups are substituted by 0 to 3 fluoro groups;
• R5 is H, C1-C6 alkyl, or phenyl substituted by groups set forth in the definition of R2;
• R6 is H, C1-C6 alkyl, C3-C8 cycloalkyl, C6-C10 aryl, or 5-10 membered heteroaryl, wherein said aryl and heteroaryl groups are substituted by 1 or 2 substituents independently selected from phenyl, groups set forth in the definition of R2, and phenyl substituted by 1 or 2 groups set forth in the definition of R2;
• which comprises treating a compound of the formula
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• or the enantiomer of said compound of formula VII in the preparation of the enantiomer of the compound of formula IX, wherein R1 and R2 are as defined above and X is halo or C1-C4 perfluoroalkylsulfonate, with a compound of the formula VIII:
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• wherein R3 is as defined above, in the presence of a base or fluoride salt and a palladium catalyst.