5-Chloro-1,3-benzodioxole → 1,3-Benzodioxole, 6-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

HRID 1490560Notes

Reaction equation

HRID 1490560 reaction equation
Clc1ccc2c(c1)OCO2>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(c2cc(Cl)cc3c2OCO3)OC1(C)C

Participants

6

Reactant 1

HCID 1389665-Chloro-1,3-benzodioxole

Product 1

HCID 1223808001,3-Benzodioxole, 6-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-Yield 96%

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
50 °C

Procedure

The general procedure B was followed using 5-chlorobenzo[d][1,3]dioxole (58.5 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 50 oC. 5p was obtained as white solid (136.3 mg, 96%) after purification by silica gel flash chromatography (EtOAc/PE=1:20 v/v) m.p.: 115-117 oC.

Sources & evidence

ORD record
ord-eb434d15819c4ae6be056040a892991c
Source dataset
Borylation dataset from Roche

Reaction notes

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