US 12,281,091 B1
Methods of preparing cannabinoids or derivatives thereof
Robert Paul Jensen, Portland, OR (US); and Vaughn Hartung, Milwaukie, OR (US)
Assigned to FloraScience Inc., Milwaukie, OR (US)
Filed by FloraScience Inc., Milwaukie, OR (US)
Filed on Jun. 11, 2024, as Appl. No. 18/739,493.
Application 18/739,493 is a continuation of application No. 18/403,509, filed on Jan. 3, 2024.
Int. Cl. C07D 311/80 (2006.01); B01J 27/06 (2006.01); C07D 307/91 (2006.01)
CPC C07D 311/80 (2013.01) [B01J 27/06 (2013.01); C07D 307/91 (2013.01)] 29 Claims
 
1. A method of preparing a compound of Formula (I):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein:
R1 is hydrogen, C1-C10 alkyl, C(═O)—(C1-C10 alkyl), or Si(C1-C10 alkyl)3;
R2 is hydrogen or C1-C10 alkyl;
R3 is hydrogen, C1-C6 alkyl, or C1-C6 hydroxyalkyl;
R4 is hydrogen, C1-C10 alkyl, or C2-C10 alkenyl;
R5 is hydrogen, C1-C10 alkyl, or C2-C10 alkenyl; and
R6 is hydrogen, C1-C6 alkyl, C(═O)(OH), or C(═O)—(C1-C6 alkyl);
the method comprising:
admixing a catalyst, an oxidizing agent, and a compound of Formula (II):

OG Complex Work Unit Chemistry
wherein each custom character is independently a single bond or a double bond, and wherein only one custom character is a double bond, to form a compound of Formula (I), or a pharmaceutically acceptable salt thereof,
wherein the catalyst is I2, Br2, or Cl2; and
the oxidizing agent comprises one or more of O2, S8, benzoquinone, chloranil, hydrogen peroxide, peracetic acid, diacetyl peroxide, ditertbutyl peroxide, dicumyl peroxide, peroxybenzoic acid, benzoyl peroxide, and dimethyl sulfoxide.