Methyl 2-Methoxybenzoate → Methyl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

HRID 1490927Notes

Reaction equation

HRID 1490927 reaction equation
COC(=O)c1ccccc1OC>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)ccc1OC.COC(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1OC

Participants

7

Reactant 1

HCID 61151Methyl 2-Methoxybenzoate

Product 2

HCID 22171502Methyl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateYield 85%HCID 22930502Methyl 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateYield 15%

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 Cwas applied to methyl 2-methoxybenzoate15c(66mg, 0.4mmol). The reaction mixture was stirredat room temperature for 16hours giving a conversion of >99% (GC-MS) and 16cand 17cin a 85:15mixture(1H NMR spectrum).

Sources & evidence

ORD record
ord-4f8c6610445e45ab8ee87e5582f3798b
Source dataset
Borylation dataset from Roche

Reaction notes

Loading…