Ethanone, 1-(2-chlorophenyl)- → HCID 75486946, compound

HRID 1490934Notes

Reaction equation

HRID 1490934 reaction equation
CC(=O)c1ccccc1Cl>C1=CCCC=CCC1.C1=CCCC=CCC1.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)ccn2)c1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.COC(C)(C)C.C[OH2+].C[OH2+].[Ir].[Ir]>CC(=O)c1cc(B2OC(C)(C)C(C)(C)O2)ccc1Cl.CC(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1Cl

Participants

7

Reactant 1

HCID 72864Ethanone, 1-(2-chlorophenyl)-

Product 2

HCID 75486946HCID 75486946, compoundYield 84%HCID 1299466451-[2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanoneYield 16%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
25 °C

Procedure

General procedure C was applied to 2-(2-chlorophenyl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane15k(96 mg, 0.4 mmol). The reaction mixture was stirredat room temperature for 16hours giving a conversion of >99% (GCMS) and monoborylated products (16k+zzarising from trace chlorobenzene impurity in the reaction mixture)and 17k in a84:16mixture (1H NMR spectrum).

Sources & evidence

ORD record
ord-18a75699f8fc40179e3bebc6eaa44775
Source dataset
Borylation dataset from Roche

Reaction notes

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