3-Bromoanisole → 2-(3-Bromo-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1490550Notes

Reaction equation

HRID 1490550 reaction equation
COc1cccc(Br)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(Br)cc(B2OC(C)(C)C(C)(C)O2)c1

Participants

6

Reactant 1

HCID 169713-Bromoanisole

Product 1

HCID 159062002-(3-Bromo-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 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
100 °C

Procedure

The general procedure A was followed using 1-bromo-3-methoxybenzene (62.5 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 at 16 hours 100 oC. 5f was obtained as colorless oil (150.3 mg, 96%) after purification by silica gel flash chromatography (EtOAc/PE=1:40 v/v).

Sources & evidence

ORD record
ord-6950785a841e41aaa681a80bf95ac547
Source dataset
Borylation dataset from Roche

Reaction notes

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