4-Bromo-2-fluorobenzonitrile → 4-Bromo-2-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

HRID 1491466Notes

Reaction equation

HRID 1491466 reaction equation
N#Cc1ccc(Br)cc1F>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)ccn2)c1.CC1(C)OBOC1(C)C.C[OH2+].C[OH2+].[Ir].[Ir]>CC1(C)OB(c2cc(Br)cc(F)c2C#N)OC1(C)C.CC1(C)OB(c2cc(C#N)c(F)cc2Br)OC1(C)C

Participants

7

Reactant 1

HCID 7360294-Bromo-2-fluorobenzonitrile

Product 2

HCID 534266394-Bromo-2-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrileYield 81%HCID 1299765514-Bromo-2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrileYield 4%

Reagents, catalysts & solvents 4

HCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Sources & evidence

ORD record
ord-5e7f3eae47f147d3b723e00940fd0e6d
Source dataset
Borylation dataset from Roche

Reaction notes

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