1-Bromo-3-(trifluoromethoxy)benzene → 3-Bromo-5-(trifluoromethoxy)phenylboronic acid pinacol ester

HRID 1490551Notes

Reaction equation

HRID 1490551 reaction equation
FC(F)(F)Oc1cccc(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>CC1(C)OB(c2cc(Br)cc(OC(F)(F)F)c2)OC1(C)C

Participants

6

Reactant 1

HCID 5199641-Bromo-3-(trifluoromethoxy)benzene

Product 1

HCID 1223807983-Bromo-5-(trifluoromethoxy)phenylboronic acid pinacol esterYield 100%

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-(trifluoromethoxy)benzene (73.5 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 100 oC. 5g was obtained as colorless oil (183.0 mg, 100%) after purification by silica gel flash chromatography (EtOAc/PE=1:30 v/v).

Sources & evidence

ORD record
ord-6f75e7603997451faa50a4b6f240d4f1
Source dataset
Borylation dataset from Roche

Reaction notes

Loading…