1-Chloro-4-(methylthio)benzene → 2-(5-Chloro-2-(methylthio)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1491137Notes

Reaction equation

HRID 1491137 reaction equation
CSc1ccc(Cl)cc1>C1=CCCC=CCC1.C1=CCCC=CCC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[OH2+].C[OH2+].Cc1ccc(C)cc1.Cc1ccnc(-c2cc(C)ccn2)c1.[Ir].[Ir]>CSc1ccc(Cl)c(B2OC(C)(C)C(C)(C)O2)c1.CSc1ccc(Cl)cc1B1OC(C)(C)C(C)(C)O1

Participants

7

Reactant 1

HCID 312431-Chloro-4-(methylthio)benzene

Product 2

HCID 1631980062-(5-Chloro-2-(methylthio)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 47%HCID 178503174HCID 178503174, compoundYield 24%

Reagents, catalysts & solvents 4

HCID 143384,4'-Dimethyl-2,2'-bipyridineReagentHCID 2733548Bis(pinacolato)diboraneReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 7809P-XyleneSolvent

Conditions

Temperature
55 °C

Procedure

dtbpy: A mixture of ortho- and meta-borylated products (102 mg, 71% yield, ortho/meta + para = 2.0); white solid;

Sources & evidence

ORD record
ord-8ca032151d194b55b61a90fc33d7cee6
Source dataset
Borylation dataset from Roche

Reaction notes

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