Ethyl 3-hydroxybenzoate → Ethyl 3-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

HRID 1490701Notes

Reaction equation

HRID 1490701 reaction equation
CCOC(=O)c1cccc(O)c1>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCCCC1.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)ccn2)c1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.CC1(C)OBOC1(C)C.C[OH2+].C[OH2+].[Ir].[Ir]>CCOC(=O)c1cc(O)cc(B2OC(C)(C)C(C)(C)O2)c1.CCOC(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)c(O)c1

Participants

8

Reactant 1

HCID 24522Ethyl 3-hydroxybenzoate

Product 2

HCID 130066909Ethyl 3-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateYield 82%HCID 131586531Ethyl 3-hydroxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateYield 18%

Reagents, catalysts & solvents 5

HCID 2733548Bis(pinacolato)diboraneReagentHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 8078CyclohexaneSolvent

Conditions

Temperature
80 °C

Sources & evidence

ORD record
ord-243778d5f5a048b2bc156278d3a99182
Source dataset
Borylation dataset from Roche

Reaction notes

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