3-Chloroanisole → 2-(3-Chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1490549Notes

Reaction equation

HRID 1490549 reaction equation
COc1cccc(Cl)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(Cl)cc(B2OC(C)(C)C(C)(C)O2)c1

Participants

6

Reactant 1

HCID 178333-Chloroanisole

Product 1

HCID 467396182-(3-Chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 97%

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-chloro-3-methoxybenzene (60.4 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. 5e was obtained as colorless oil (130.2 mg, 97%) after purification by silica gel flash chromatography (EtOAc/PE=1:40 v/v).

Sources & evidence

ORD record
ord-617630db07554c4f9a1fe7f460f7cdc9
Source dataset
Borylation dataset from Roche

Reaction notes

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