1-Methoxy-4-(methylthio)benzene → 2-(2-Methoxy-5-methylsulfanylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1491133

Reaction equation

HRID 1491133 reaction equation
COc1ccc(SC)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]>COc1ccc(SC)c(B2OC(C)(C)C(C)(C)O2)c1.COc1ccc(SC)cc1B1OC(C)(C)C(C)(C)O1

Participants

7

Reactant 1

HCID 158851-Methoxy-4-(methylthio)benzene

Product 2

HCID 1315155222-(2-Methoxy-5-methylsulfanylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 32%HCID 1325102602-(5-Methoxy-2-methylsulfanylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 31%

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 (88 mg, 63% yield, ortho/meta + para = 1.0); yellow solid;

Sources & evidence

ORD record
ord-c647f1265df44679848754ba33bea1e4
Source dataset
Borylation dataset from Roche

Linked notes

Loading…