Dimethyl isophthalate → Dimethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,3-dicarboxylate

HRID 1490555Notes

Reaction equation

HRID 1490555 reaction equation
COC(=O)c1cccc(C(=O)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>COC(=O)c1cc(B2OC(C)(C)C(C)(C)O2)cc(C(=O)OC)c1

Participants

6

Reactant 1

HCID 15088Dimethyl isophthalate

Product 1

HCID 42614529Dimethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,3-dicarboxylateYield 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 dimethyl isophthalate (97.1 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 16 hours at 100 oC. 5k was obtained as white solid (151.1 mg, 95%) after purification by silica gel flash chromatography (EtOAc/PE=1:15 v/v). m.p.: 126-127 oC.

Sources & evidence

ORD record
ord-5dc4a3574eaf41f4b2775be895690305
Source dataset
Borylation dataset from Roche

Reaction notes

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