Hydrochloric Acid → (3-Bromo-5-formylphenyl)boronic acid

HRID 487070Notes

Reaction equation

HRID 487070 reaction equation
C([Li])CCC.[Br:6][C:7]1[CH:8]=[C:9]([CH:14]([O:17]C)OC)[CH:10]=[C:11](Br)[CH:12]=1.[B:19](OC(C)C)([O:24]C(C)C)[O:20]C(C)C.Cl>CCOCC>[Br:6][C:7]1[CH:12]=[C:11]([B:19]([OH:24])[OH:20])[CH:10]=[C:9]([CH:14]=[O:17])[CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 190934581,3-Dibromo-5-(dimethoxymethyl)benzeneHCID 178418339Butyllithium

Product 1

HCID 19093459(3-Bromo-5-formylphenyl)boronic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4.2 mL (10.5 mmoles) of 2.5 m n-butyllithium was added to a solution of 3.1 g (10.5 mmoles) of 3,5-dibromo(dimethoxymethyl)benzene in 50 mL of ether at -78° under nitrogen over a period of 2 minutes. The reaction mixture was stirred 8 minutes and 2.415 mL (10.5 mmoles) of triisopropyl borate was added. The reaction was stirred 5.5 hrs at room temperature after cooling to 0°, 21 mL of 2N hydrochloric acid was added. After stirring 1 hour at room temperature, ether layer was separated and washed with saturated sodium chloride solution. After drying over anhydrous MgSO4, solvent was removed to give a solid, which was triturated with petroleum ether. The resulting solid was dried in vacuo to give the desired boronic acid.

Workup

  1. stirringThe reaction was stirred 5.5 hrs at room temperature
  2. temperatureafter cooling to 0°
  3. stirringAfter stirring 1 hour at room temperature
  4. customether layer was separated
  5. washwashed with saturated sodium chloride solution
  6. dry with materialAfter drying over anhydrous MgSO4, solvent
  7. customwas removed
  8. customto give a solid, which
  9. customwas triturated with petroleum ether
  10. customThe resulting solid was dried in vacuo

Sources & evidence

ORD record
ord-8665fe94580a483b9ef366dbbb9e6543
Source dataset
uspto-grants-1994_03
Patent number
US05294610

Reaction notes

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