3-Bromobenzonitrile → 3-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

HRID 1490562Notes

Reaction equation

HRID 1490562 reaction equation
N#Cc1cccc(Br)c1>C1=CCCC=CCC1.C1=CCCC=CCC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.COC1CCCC1.C[OH2+].C[OH2+].[Ir].[Ir].c1ccc(N2B(B3Nc4ccccc4N3c3ccccn3)Nc3ccccc32)nc1>CC1(C)OB(c2cc(Br)cc(C#N)c2)OC1(C)C

Participants

6

Reactant 1

HCID 233813-Bromobenzonitrile

Product 1

HCID 114040463-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrileYield 55%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 1223807993-pyridin-2-yl-2-(3-pyridin-2-yl-1H-1,3,2-benzodiazaborol-2-yl)-1H-1,3,2-benzodiazaboroleReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 138539Cyclopentyl methyl etherSolvent

Conditions

Temperature
125 °C

Procedure

The general procedure A was followed using 3-bromobenzonitrile (91.0 mg, 0.5 mmol) and B2pin2 (126.9 mg, 0.75 mmol, 1.5 eq.) as starting material. The resulting mixture was allowed to stir 48 hours at 125 oC. 5r was obtained as white solid (85.2 mg, 55%) after purification by silica gel flash chromatography (EtOAc/PE=1:15 v/v). m.p.: 81-83 oC.

Sources & evidence

ORD record
ord-e6f10914d6d7482292ff5149d3753b3f
Source dataset
Borylation dataset from Roche

Reaction notes

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