3-Bromotoluene → 2-(3-Bromo-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1491372Notes

Reaction equation

HRID 1491372 reaction equation
Cc1cccc(Br)c1>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCc2c(c3c(c4c2CCCC4)CCCC3)C1.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)ccn2)c1.CC1(C)OBOC1(C)C.C[OH2+].C[OH2+].ClCCl.[Ir].[Ir]>Cc1cc(Br)cc(B2OC(C)(C)C(C)(C)O2)c1

Participants

7

Reactant 1

HCID 115603-Bromotoluene

Product 1

HCID 534290562-(3-Bromo-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 11%

Reagents, catalysts & solvents 5

HCID 95278DodecahydrotriphenyleneReagentHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Sources & evidence

ORD record
ord-45d2d8de0f4b48c2b9310e1fc3f8e370
Source dataset
Borylation dataset from Roche

Reaction notes

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