1,2,3-Trimethoxybenzene → 4,4,5,5-Tetramethyl-2-(3,4,5-trimethoxyphenyl)-1,3,2-dioxaborolane

HRID 1490545Notes

Reaction equation

HRID 1490545 reaction equation
COc1cccc(OC)c1OC>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(B2OC(C)(C)C(C)(C)O2)cc(OC)c1OC

Participants

6

Reactant 1

HCID 124621,2,3-Trimethoxybenzene

Product 1

HCID 219239464,4,5,5-Tetramethyl-2-(3,4,5-trimethoxyphenyl)-1,3,2-dioxaborolaneYield 99%

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 1,2,3-trimethoxybenzene (84.1 mg, 0.5 mmol) and B2pin2 (126.9 mg, 0.5 mmol, 1.0 eq.) as starting material. The resulting mixture was allowed to stir 8 hours at 100 oC. 5c was obtained as white solid (146.1 mg, 99%) after purification by silica gel flash chromatography (EtOAc/PE=1:20 v/v). m.p.: 104-106 °C.

Sources & evidence

ORD record
ord-a6ca3c63c73e4b2988f631e8660d014c
Source dataset
Borylation dataset from Roche

Reaction notes

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