2-Bromo-5-fluorotoluene → HCID 56973146, compound

HRID 1490559Notes

Reaction equation

HRID 1490559 reaction equation
Cc1cc(F)ccc1Br>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>Cc1cc(F)c(B2OC(C)(C)C(C)(C)O2)cc1Br

Participants

6

Reactant 1

HCID 967432-Bromo-5-fluorotoluene

Product 1

HCID 56973146HCID 56973146, compoundYield 100%

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-4-fluoro-2-methylbenzene (61.5 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. 5o was obtained as white solid (158.0 mg, 100%) after purification by silica gel flash chromatography (EtOAc/PE=1:30 v/v). m.p.: 72-74 oC.

Sources & evidence

ORD record
ord-76991da0fd3a4e81917b8653883cc894
Source dataset
Borylation dataset from Roche

Reaction notes

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