3-Bromothioanisole → HCID 138982948, compound

HRID 1491156Notes

Reaction equation

HRID 1491156 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.FC(F)(F)C1COB(c2ccccc2-c2ccc(-c3ccccn3)nc2)O1.[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 10%HCID 138982948HCID 138982948, compoundYield 69%

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 (130 mg, 79% yield, ortho/meta + para = 6.7); ortho-borylated product 4o was obtained by further purification by GPC (96 mg, 59% yield), colorless oil;

Sources & evidence

ORD record
ord-e20e8efc8090420da8fb44189d3d0c23
Source dataset
Borylation dataset from Roche

Reaction notes

Loading…