Back to results
US 2023/0183157 A1Published application
Processes for the preparation of halogenated dihydroxybenzene compounds
AssigneePurisys LLC
InventorsDaniel M. HALLOW, Mark C. DOBISH, Gnel MKRTCHYAN, Richard WOOD, Ramanaiah C. KANAMARLAPUDI, Achintya SUJAN, Amber BURCH
Life of this patent
Estimating the term…
Abstract
The present disclosure relates to the preparation of halogenated dihydroxybenzene compounds with high yield, selectivity and purity. The compounds are useful, among other things, in the synthesis of cannabinoids and cannabinoid-type compounds.
Claims31
A method of preparing a compound of Formula I:
- wherein,
- R1 is a branched or straight chain C1-12 alkyl;
- and
- R2 and R3 are each independently selected from a group consisting of halogen, —C(O)O—C1-6 alkyl, and hydrogen, wherein at least one of R2 and R3 is halogen, the method comprising:
- contacting a compound of Formula I′ having a structure:
- wherein, R1′ is a branched or straight chain C1-12 alkyl;
- and
- R2′ and R3′ are each independently selected from the group consisting of halogen, —C(O)O—C1-6 alkyl, and hydrogen, wherein at least one of R2′ and R3′ is hydrogen;
- with HX, wherein X is a halide, in the presence of an organic sulfoxide
- wherein, the contacting is at a temperature from about 0° C. to about 100° C.;
- and
- wherein, the compound of Formula I is prepared.
9 more elements
-4. (canceled)
(canceled)
-11. (canceled)
-14. (canceled)
(canceled)
(canceled)
-26. (canceled)
A method of preparing a compound of Formula I:
- wherein,
- R1 is a branched or straight chain C1-12 alkyl;
- and
- R2 and R3 are each halogen,
- the method comprising:
- selectively halogenating at the 4- and 6-positions by contacting a compound of Formula I′ having a structure:
- wherein, R1′ is a branched or straight C1-12 alkyl;
- and
- R2′ and R3′ are each hydrogen;
- with a first solvent to form a mixture,
- contacting the mixture with HX, wherein X is a halide, in the presence of an organic sulfoxide;
- wherein, the contacting is at a temperature from about 0° C. to about 100° C.;
- and
- wherein, the compound of Formula I is prepared.
11 more elements
-30. (canceled)
-35. (canceled)
-39. (canceled)
A composition comprising 4,6-DBO;
- 4-MBO;
- 2,4-DBO and TBO in amounts of about 94%, about 3%, about 1%, and about 1%, respectively.
-43. (canceled)
Dependencies are inferred from the claim text.