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

HRID 1491138Notes

Reaction equation

HRID 1491138 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.FC(F)(F)C1COB(c2ccccc2-c2ccc(-c3ccccn3)nc2)O1.[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 74%HCID 178503104HCID 178503104, compoundYield 11%

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 (139 mg, 85% yield, ortho/meta + para = 6.6); ortho-borylated product 4f was obtained by further purification by GPC (101 mg, 62% yield), yellow solid (mp. 88-90 oC)

Sources & evidence

ORD record
ord-344f37acfe63498da614c14da31d0868
Source dataset
Borylation dataset from Roche

Reaction notes

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