1-Bromo-3,5-difluorobenzene → 2-(4-BroMo-2,6-difluoro-phenyl)-4,4,5,5-tetraMethyl-[1,3,2]dioxaborolane

HRID 1490557Notes

Reaction equation

HRID 1490557 reaction equation
Fc1cc(F)cc(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(c2c(F)cc(Br)cc2F)OC1(C)C

Participants

6

Reactant 1

HCID 1363131-Bromo-3,5-difluorobenzene

Product 1

HCID 592439462-(4-BroMo-2,6-difluoro-phenyl)-4,4,5,5-tetraMethyl-[1,3,2]dioxaborolaneYield 87%

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
100 °C

Procedure

The general procedure A was followed using 1-bromo-3,5-difluorobenzene (57.0 uL, 0.5 mmol) and B2pin2 (126.9 mg, 0.5 mmol, 1.0 eq.) as starting material. The resulting mixture was allowed to stir 16 hours at 100 oC. 5m was obtained as colorless oil (138.2 mg, 87%) after purification by silica gel flash chromatography (EtOAc/PE=1:10 v/v).

Sources & evidence

ORD record
ord-3a6b42f75f804a2aba1f37cf8826e9a3
Source dataset
Borylation dataset from Roche

Reaction notes

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