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

HRID 1490696Notes

Reaction equation

HRID 1490696 reaction equation
CCOC(=O)c1cccc(O)c1>C1=CCCC=CCC1.C1=CCCC=CCC1.C1COB(B2OCCO2)O1.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)ccn2)c1.CC(C)(O)C(C)(C)O.CCN(CC)CC.C[OH2+].C[OH2+].Cc1ccccc1.ClC(Cl)Cl.[Ir].[Ir]>CCOC(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)c(O)c1

Participants

9

Reactant 1

HCID 24522Ethyl 3-hydroxybenzoate

Product 1

HCID 131586531Ethyl 3-hydroxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateYield 56%

Reagents, catalysts & solvents 7

HCID 6425PinacolReagentHCID 8471TriethylamineReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylReagentHCID 186732542,2'-Bi-1,3,2-dioxaborolaneReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 1140TolueneSolventHCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Sources & evidence

ORD record
ord-a81f942d893d4c9bb4112bf5379f735f
Source dataset
Borylation dataset from Roche

Reaction notes

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