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US 10,399,917 B2Granted
Process for the preparation of organic bromides
AssigneeTechnion Research & Development Foundation Limited
InventorsMark Gandelman, Gennady Nisnevich, Kseniya Kulbitski, Alexander Artaryan
Life of this patent
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Abstract
The present invention provides a process for the preparation of organic bromides, by a radical bromodecarboxylation of carboxylic acids with a bromoisocyanurate.
Claims36
A process for the preparation of organic bromide of formula (1A) from a carboxylic acid of formula (2A) represented by scheme 1:
- said process comprises radical bromodecarboxylation reaction of carboxylic acid (2A) with a bromoisocyanurate to yield organic bromide (1A);
- wherein
- said bromoisocyanurate is tribromoisocyanuric acid, dibromoisocyanuric acid, bromodichloroisocyanuric acid, dibromochloroisocyanuric acid, bromochloroisocyanuric acid, or any combination thereof;
- A is arene, alkane, cycloalkane or saturated heterocycle;
- n is an integer of at least 1;
- m is an integer of at least 0;
- and
- each Q is independently F, Cl, Br, R1, acyl, C(O)R1, C(O)OR1, C(O)Cl, C(O)N(R1)2, CN, SO2R1, SO3R1, NO2, N(R1)3+, OR1, OCF3, O-acyl, OC(O)R1, OSO2R1, SR1, S-acyl, SC(O)R1, N(R1)acyl, N(R1)C(O)R1, N(R1)SO2R1, N(acyl)2, N[C(O)R1]SO2R1, N[C(O)R1]2, CF3;
- or any two vicinal Q substituents are joined to form a 5- or 6-membered substituted or unsubstituted, saturated or unsaturated carbocyclic or heterocyclic ring;
- wherein each R1 is independently aryl, alkyl, cycloalkyl or heterocyclyl, wherein said R1 is optionally substituted by one or more substituents of R2;
- wherein each R2 is independently F, Cl, Br, COOH, acyl, aryl, alkyl, cycloalkyl or heterocyclyl;
- wherein if either one of R2 in (2A) is carboxylic group COOH, then the respective R2 in (1A) is Br;
- wherein the position of said Br and Q in said structure of formula (1A) correspond to the same position of said COOH and Q, respectively in said structure of formula (2A).
10 more elements
A radiation-sensitive composition comprising carboxylic acid of formula (2A)
- and bromoisocyanurate which generates organic bromide of formula (1A)
- upon electromagnetic irradiation,
- wherein
- the bromoisocyanurate is tribromoisocyanuric acid, dibromoisocyanuric acid, bromodichloroisocyanuric acid, dibromochloroisocyanuric acid, bromochloroisocyanuric acid, or any combination thereof;
- A is arene, alkane, cycloalkane or saturated heterocycle;
- n is an integer of at least 1;
- m is an integer of at least 0;
- each Q is independently F, Cl, Br, R1, acyl, C(O)R1, C(O)OR1, C(O)OMe, C(O)Cl, C(O)N(R1)2, CN, SO2R1, SO3R1, NO2, N(R1)3+, OR1, OCF3, O-acyl, OC(O)R1, OSO2R1, SR1, S-acyl, SC(O)R1, N(R1)acyl, N(R1)C(O)R1, N(R1)SO2R1, N(acyl)2, N[C(O)R1]SO2R1, N[C(O)R1]2, CF3;
- or any two vicinal Q substituents are joined to form a 5- or 6-membered substituted or unsubstituted, saturated or unsaturated carbocyclic or heterocyclic ring;
- wherein each R1 is independently aryl, alkyl, cycloalkyl or heterocyclyl, wherein R1 is optionally substituted by one or more substituents of R2;
- wherein each R2 is independently F, Cl, Br, COOH, acyl, aryl, alkyl, cycloalkyl or heterocyclyl;
- wherein if either one of R2 in (2A) is a carboxylic group COOH, then the respective R2 in (1A) is Br;
- wherein the position of said Br and Q in said structure of formula (1A) correspond to the same position of said COOH and Q, respectively in said structure of formula (2A).
10 more elements
Dependencies are inferred from the claim text.