Triisopropyl borate → (2,6-Dimethylpyridin-4-yl)boronic acid

HRID 1038065Notes

Reaction equation

HRID 1038065 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH3:9])[CH:3]=1.[B:10](OC(C)C)([O:15]C(C)C)[O:11]C(C)C.[Li]CCCC>C1COCC1>[CH3:8][C:6]1[CH:7]=[C:2]([B:10]([OH:15])[OH:11])[CH:3]=[C:4]([CH3:9])[N:5]=1

Participants

5

Reactant 3

HCID 21531Triisopropyl borateHCID 130817354-Bromo-2,6-dimethylpyridineHCID 178418339Butyllithium

Product 1

HCID 23546910(2,6-Dimethylpyridin-4-yl)boronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Bromo-2,6-dimethyl-pyridine (910 mg, 4.9 mmol) and triisopropyl borate (2.3 mL, 10 mmol) in THF (10 mL) were cooled in a −78° C. bath. BuLi (2.7 M, 7 mL) was added in drop wise. After 3 hrs, the bath was removed. The reaction was acidified with 1N HCl till pH=1. The separated aqueous layer was neutralized with NaOH and subsequently extracted with ethyl acetate. A crude white solid was obtained (800 mg) as the title compound.

Workup

  1. customthe bath was removed
  2. extractionsubsequently extracted with ethyl acetate

Sources & evidence

ORD record
ord-70c2b3acf9cc41d79e2de41243a555de
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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