Hydrochloric Acid → 4-Pivalamidophenylboronic acid

HRID 496118Notes

Reaction equation

HRID 496118 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:5]([NH:6][C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[Li]C(C)(C)C.[B:20](OC)([O:23]C)[O:21]C.Cl>C1COCC1>[CH3:9][C:8]([CH3:11])([CH3:10])[C:7]([NH:6][C:5]1[CH:13]=[CH:14][C:2]([B:20]([OH:23])[OH:21])=[CH:3][CH:4]=1)=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 520094N-(4-Bromophenyl)-2,2-dimethylpropanamideHCID 178418306HCID 178418306, compound

Product 1

HCID 223240854-Pivalamidophenylboronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 4-bromo-N-pivaloylaniline (1.56 g, 6 mmol) in dry THF (50 ml) at −78° C. was added t-BuLi (1.5 M in pentane, 13.3 ml, 20 mmol) and the yellow mixture was stirred for 1 h at −78° C. under N2. The reaction was quenched with B(OCH3)3 (1.7 ml, 15 mmol) and stirred for another 1 h at −78° C. The reaction mixture was then warmed to room temperature and hydrolysed with 0.5 M hydrochloric acid (50 ml) and extracted with EtOAc (3×80 ml), dried (Na2SO4) and concentrated to ca. 40 ml. n-Hexane (120 ml) was added slowly and the colorless crystalline product was filtered off and dried, yielding 1.26 g (95%).

Workup

  1. stirringstirred for another 1 h at −78° C
  2. extractionextracted with EtOAc (3×80 ml)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated to ca. 40 ml
  5. additionn-Hexane (120 ml) was added slowly
  6. filtrationthe colorless crystalline product was filtered off
  7. customdried
  8. customyielding 1.26 g (95%)

Sources & evidence

ORD record
ord-623e775ec87a48e0b74d0d731fc70272
Source dataset
uspto-grants-2005_09
Patent number
US06943159B1

Reaction notes

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