Triisopropyl borate → (5-Bromo-2-(diisopropylcarbamoyl)phenyl)boronic acid

HRID 2193000Notes

Reaction equation

HRID 2193000 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([N:8]([CH:12]([CH3:14])[CH3:13])[CH:9]([CH3:11])[CH3:10])=[O:7])=[CH:4][CH:3]=1.[B:17](OC(C)C)([O:22]C(C)C)[O:18]C(C)C.[Li+].CC([N-]C(C)C)C>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]([CH:12]([CH3:14])[CH3:13])[CH:9]([CH3:10])[CH3:11])=[O:7])=[C:15]([B:17]([OH:22])[OH:18])[CH:16]=1

Participants

5

Reactant 3

HCID 21531Triisopropyl borateHCID 2724682Lithium diisopropylamideHCID 36169884-Bromo-N,N-diisopropylbenzamide

Product 1

HCID 59375409(5-Bromo-2-(diisopropylcarbamoyl)phenyl)boronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-bromo-N,N-diisopropylbenzamide (1.0 g, 35 mmol) and triisopropyl borate (0.79 g, 4.2 mmol) in THF (20 mL) was added a freshly prepared solution of LDA in THF (4.6 mL, 4.6 mmol) dropwise at 20° C. over a 1 hour period under nitrogen. The reaction mixture was stirred overnight, quenched with saturated aqueous NH4Cl solution (20 mL), and extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with brine (20 mL), dried over magnesium sulfate, filtered and concentrated to afford {5-bromo-2-[(diisopropylamino)carbonyl]phenyl}boronic acid that was used without further purification.

Workup

  1. customquenched with saturated aqueous NH4Cl solution (20 mL)
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. washThe combined organic layers were washed with brine (20 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4682e82fcfef4f8fa28a55e22223d1ed
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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