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US 12,291,525 B2Granted
Process for synthesis of a 2-(5-isoxazolyl)-phenol
AssigneeFMC Corporation
InventorsJunbae Hong, Joerg Bruening
Life of this patent
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Abstract
A method for preparing a compound of Formula (1) and compounds therefrom, comprising treating a compound of Formula (2) to provide a compound of Formula (5) and treating the compound of Formula (5) with a hydroxylamine salt wherein R1, R2 and m are as defined in the specification. The compound of Formula (1), prepared by the above method, can be used to prepare a compound of Formula (8) wherein R1, R2, R3 and m are as defined in the specification.
Claims20
A method for preparing a compound of Formula 1
- wherein
- each R1 is independently halogen, cyano, C1-C4 alkyl or C1-C4 haloalkyl;
- R2 is cyano, C1-C4 alkyl or C1-C4 haloalkyl;
- and
- m is 0, 1, 2 or 3;
- the method comprising
- treating a compound of Formula 2
- wherein
- each R1 is independently halogen, cyano, C1-C4 alkyl or C1-C4 haloalkyl;
- m is 0, 1, 2 or 3;
- and
- X is halogen;
- with a compound of Formula 3
- R2(C═O)LG 3
- wherein
- R2 is cyano, C1-C4 alkyl or C1-C4 haloalkyl;
- and
- LG is chloro, C1-C4 alkoxy or —O(C═O)R2
- in the presence of an alkali metal base to provide a compound of Formula 4 or an alkali metal salt thereof
- wherein
- each R1 is independently halogen, cyano, C1-C4 alkyl or C1-C4 haloalkyl;
- R2 is cyano, C1-C4 alkyl or C1-C4 haloalkyl;
- m is 0, 1, 2 or 3;
- and
- X is halogen;
- heating the compound of Formula 4 or the alkali metal salt thereof to provide a compound of Formula 5
- wherein
- each R1 is independently halogen, cyano, C1-C4 alkyl or C1-C4 haloalkyl;
- R2 is cyano, C1-C4 alkyl or C1-C4 haloalkyl;
- and
- m is 0, 1, 2 or 3;
- treating the compound of Formula 5 with a hydroxylamine salt to provide a compound of Formula 6
- wherein
- each R1 is independently halogen, cyano, C1-C4 alkyl or C1-C4 haloalkyl;
- R2 is cyano, C1-C4 alkyl or C1-C4 haloalkyl;
- and
- m is 0, 1, 2 or 3;
- and
- treating the compound of Formula 6 with acid.
36 more elements
A method for preparing a compound of Formula 8
- wherein
- each R1 is independently halogen, cyano, C1-C4 alkyl or C1-C4 haloalkyl;
- R2 is cyano, C1-C4 alkyl or C1-C4 haloalkyl;
- R3 is halogen, C1-C4 alkyl or C1-C4 haloalkyl;
- and
- m is 0, 1, 2 or 3;
- the method comprising
- treating a compound of Formula 2
- wherein
- each R1 is independently halogen, cyano, C1-C4 alkyl or C1-C4 haloalkyl;
- m is 0, 1, 2 or 3;
- and
- X is halogen;
- with a compound of Formula 3
- R2(C═O)LG 3
- wherein
- R2 is cyano, C1-C4 alkyl or C1-C4 haloalkyl;
- and
- LG is chloro, C1-C4 alkoxy or —O(C═O)R2
- in the presence of a base to provide a salt of a compound of Formula 4
- wherein
- each R1 is independently halogen, cyano, C1-C4 alkyl or C1-C4 haloalkyl;
- R2 is cyano, C1-C4 alkyl or C1-C4 haloalkyl;
- m is 0, 1, 2 or 3;
- and
- X is halogen;
- heating the salt of the compound of Formula 4 to provide a compound of Formula 5
- wherein
- each R1 is independently halogen, cyano, C1-C4 alkyl or C1-C4 haloalkyl;
- R2 is cyano, C1-C4 alkyl or C1-C4 haloalkyl;
- and
- m is 0, 1, 2 or 3;
- treating the compound of Formula 5 with a hydroxylamine salt to provide a compound of Formula 6
- wherein
- each R1 is independently halogen, cyano, C1-C4 alkyl or C1-C4 haloalkyl;
- R2 is cyano, C1-C4 alkyl or C1-C4 haloalkyl;
- and
- m is 0, 1, 2 or 3;
- treating the compound of Formula 6 with acid to provide a compound of Formula 1
- wherein
- each R1 is independently halogen, cyano, C1-C4 alkyl or C1-C4 haloalkyl;
- R2 is cyano, C1-C4 alkyl or C1-C4 haloalkyl;
- and
- m is 0, 1, 2 or 3;
- and
- treating the compound of Formula 1 with a compound of Formula 7
- wherein
- Z is halogen or SO2R4;
- R3 is halogen, C1-C4 alkyl or C1-C4 haloalkyl;
- R4 is C1-C4 alkyl
- in the presence of a second base.
48 more elements
A compound of Formula 5A
- wherein
- R1 is halogen, cyano, C1-C4 alkyl or C1-C4 haloalkyl;
- and
- R2 is C1-C2 haloalkyl;
- wherein when R1 is fluoro, R2 is other than trifluoromethyl.
2 more elements
Dependencies are inferred from the claim text.