3-Bromothioanisole → 2-[3-Bromo-5-(methylsulfanyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1491157Notes

Reaction equation

HRID 1491157 reaction equation
CSc1cccc(Br)c1>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]>CSc1cc(Br)cc(B2OC(C)(C)C(C)(C)O2)c1.CSc1cc(Br)ccc1B1OC(C)(C)C(C)(C)O1

Participants

7

Reactant 1

HCID 27356273-Bromothioanisole

Product 2

HCID 532171302-[3-Bromo-5-(methylsulfanyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 63%HCID 138982948HCID 138982948, compoundYield 9%

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 (118 mg, 72% yield, ortho/meta + para = 0.13); meta-Isomer 5o was obtained by further purification of the crude mixture by GPC (86 mg, 52% yield), yellow oil;

Sources & evidence

ORD record
ord-cc0c57e9ba0a48099ad2bf31d9104279
Source dataset
Borylation dataset from Roche

Reaction notes

Loading…