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Methyl o-toluate → Methyl 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

HRID 1490932
Notes
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Reaction equation

HRID 1490932 reaction equation
COC(=O)c1ccccc1C>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]>COC(=O)c1cc(B2OC(C)(C)C(C)(C)O2)ccc1C.COC(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1C
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 1

HCID 33094Methyl o-toluate

Product 2

HCID 22930450Methyl 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateYield 27%HCID 24824346Methyl 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateYield 73%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridyl

Conditions

Temperature
25 °C

Procedure

General procedure D was applied to methyl 2-methylbenzoate15h(30 mg, 0.2 mmol). The reaction mixture was allowed to stand for 16hoursgiving a conversion of >99%(GC-MS) and 16hand 17hin a 73:27 mixture (1H NMR spectrum).

Sources & evidence

ORD record
ord-19c4d9b183614cef9fce523033f6b00a
Source dataset
Borylation dataset from Roche
DOI
10.1039/c2sc20776a

Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes
Reagent
HCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalyst
HCID 15413tert-Butyl methyl etherSolvent