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

HRID 1491136

Reaction equation

HRID 1491136 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.FC(F)(F)C1COB(c2ccccc2-c2ccc(-c3ccccn3)nc2)O1.[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 74%HCID 178503174HCID 178503174, compoundYield 6%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 1349566232-Pyridin-2-yl-5-[2-[4-(trifluoromethyl)-1,3,2-dioxaborolan-2-yl]phenyl]pyridineReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 7809P-XyleneSolvent

Conditions

Temperature
55 °C

Procedure

Ligand 3f: A mixture of ortho- and meta-borylated products (114 mg, 80% yield, ortho/meta + para = 12); ortho-borylated product 4e was obtained by further purification by GPC (70 mg, 49% yield), white solid (mp. 80-82 oC);

Sources & evidence

ORD record
ord-903f8118d14f42ecaa64e874e6518ce2
Source dataset
Borylation dataset from Roche

Linked notes

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