Synthesis of pentafluorosulfanylnaphthalene
AssigneeAir Products and Chemicals, Inc.
InventorsGauri Lal, Kristen Minnich
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Abstract
This invention relates to 2-pentafluorosulfanylnapthalene, substituted derivatives thereof and to a process for producing naphthalene carrying an SF5 group. A 3-step process is employed wherein 1,4-dihydronaphthalene is reacted with pentafluorosulfanyl halide. Next the resulting 3-halo-2-pentafluorosulfanylnaphthalene or derivative is converted to 2-pentafluorosulfanyl-1,4-dihydronaphthalene or derivative by treatment with a base and subsequently transformed into pentafluorosulfanylnaphthalene by removing hydrogen atoms.
Claims18
A compound represented by the formula:
- wherein R1-4 are H, C1-6 alkyl, substituted C1-6alkyl, aryl or substituted aryl;
- O, S, and N hetero, —COOR7 where R7 is C1-6 alkyl, —COR8 where R8 is C1-6 alkyl;
- F, Cl, Br, I;
- boron C1-6 alkyl ester, (R9)3B where R9 is C1-6 alkyl, and R5 and R6 are H.
A compound selected from the group consisting of 6-bromo-2-pentafluorosulfanylnaphthalene, 6-chloro-2-pentafluorosulfanylnaphthalene, 6-fluoro-2-pentafluorosulfanylnaphthalene, 6-iodo-2-pentafluorosulfanylnaphthalene, 6-methyl-2-pentafluorosulfanylnaphthalene, 6-propyl-2-pentafluorosulfanyinaphthalene, 6-pentyl-2-pentafluorosulfanyinaphthalene, 6-cyclohexyl-2-pentafluorosulfanylnaphthalene, 6-(4-propylcyclohexyl)-2-pentafluorosulfanyinaphthalene, 6-carboethoxy-2-pentafluorosulfanylnaphthalene, 6-trimethylsilyl-2-pentafluorosulfanylnaphthalene, 6-trimethoxyborane-2-pentafluorosulfanylnaphthalene, and 6-trimethylborane-2-pentafluorosulfanylnaphthalene.
A process for producing a compound of the formula A:
- wherein R1-4 are H, C1-6 alkyl, substituted C1-6 alkyl, aryl or substituted aryl;
- O, S, and N hetero, —COOR7 where R7 is C1-6 alkyl, —COR8 where R8 is C1-6 alkyl;
- F, Cl. Br, and I;
- boron C1-6 esters, (R9)3B where R9 is C1-6 alkyl, and R5 and R6 are H which comprises the steps:
- (a) contacting a reactant of the formula B:
- wherein R1-4 are H, C1-6 alkyl, substituted C1-6 alkyl, aryl or substituted aryl;
- O, S, and N hetero, —COOR7 where R7 is C1-6 alkyl, —COR8 where R8 is C1-6 alkyl;
- F, Cl. Br, and I;
- boron C1-6 esters, (R9)3B where R9 is C1-6 alkyl, and R5 and R5 are H with an SF5 bromide under conditions for forming compound C:
- wherein R1-4 are H, C1-6 alkyl, substituted C1-6 alkyl, aryl or substituted aryl;
- O, S, and N hetero, —COOR7 where R7 is C1-6 alkyl, —COR8 where R8 is C1-6 alkyl;
- F, Cl. Br, and I;
- boron C1-6 esters, (R9)3B where R9 is C1-6 alkyl, and R5 and R6 are H;
- (b) dehydrobrominating compound C under conditions for forming compound D having the formula:
- and then;
- (c) removing hydrogen from compound D under conditions for producing compound A.
A process for producing 2-pentafluorosulfanylnaphthalene which comprises the steps.
- (a) contacting 1,4-dihydronaphthalene with SF5Br in the presence of a catalyst to form 3-bromo-2-pentafluorosulfanylnaphthalene;
- (b) removing bromine from the compound 3-bromo-2-pentafluorosulfanylnaphthalene formed in step (a) thus forming pentafluorosulfanyl-1,4-dihydronaphthalene;
- and,
- (c) removing two hydrogen atoms from the thus formed pentafluorosulfanyl-1,4-dihydronaphthalene in step (b) to produce 2-pentafluorosulfanylnaphthalene.
Dependencies are inferred from the claim text.