3'-Bromoacetophenone → HCID 178465858, compound

HRID 1490561Notes

Reaction equation

HRID 1490561 reaction equation
CC(=O)c1cccc(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>CC(=O)c1cc(Br)cc(B2OC(C)(C)C(C)(C)O2)c1

Participants

6

Reactant 1

HCID 165023'-Bromoacetophenone

Product 1

HCID 178465858HCID 178465858, compoundYield 62%

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
150 °C

Procedure

The general procedure A was followed using 1-(3-bromophenyl)ethanone (67.9 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 150 oC. 5q was obtained as white solid (101.1 mg, 62%) after purification by silica gel flash chromatography (EtOAc/PE=1:30 v/v). m.p.: 82-84 oC.

Sources & evidence

ORD record
ord-0df2332035b54748b7ae7ffafed6e61e
Source dataset
Borylation dataset from Roche

Reaction notes

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