4-Bromothioanisole → 2-(5-Bromo-2-methylsulfanylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1491139

Reaction equation

HRID 1491139 reaction equation
CSc1ccc(Br)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(Br)c(B2OC(C)(C)C(C)(C)O2)c1.CSc1ccc(Br)cc1B1OC(C)(C)C(C)(C)O1

Participants

7

Reactant 1

HCID 660374-Bromothioanisole

Product 2

HCID 1325102612-(5-Bromo-2-methylsulfanylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 57%HCID 178503104HCID 178503104, compoundYield 19%

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 (125 mg, 76% yield, ortho/meta + para = 3.0); yellow oil;

Sources & evidence

ORD record
ord-599a909af57c4391868aa64e3ee286a1
Source dataset
Borylation dataset from Roche

Linked notes

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