1,3-Dimethoxybenzene → 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1490546Notes

Reaction equation

HRID 1490546 reaction equation
COc1cccc(OC)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>COc1cc(OC)cc(B2OC(C)(C)C(C)(C)O2)c1

Participants

6

Reactant 1

HCID 90251,3-Dimethoxybenzene

Product 1

HCID 162176602-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 95%

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 1,3-dimethoxybenzene (65.5 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. 5a was obtained as white solid (125.1 mg, 95%) after purification by silica gel flash chromatography (EtOAc/PE=1:30 v/v). m.p.: 87-88 °C

Sources & evidence

ORD record
ord-41991f4d03d44001bf614e3efe3cd16b
Source dataset
Borylation dataset from Roche

Reaction notes

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