Dimethylformamide → 4-Methoxycarbonylphenylboronic acid

HRID 382058Notes

Reaction equation

HRID 382058 reaction equation
C[Si](C=[N+]=[N-])(C)C.[C:8]([C:11]1[CH:16]=[CH:15][C:14]([B:17]([OH:19])[OH:18])=[CH:13][CH:12]=1)([OH:10])=[O:9].[CH3:20]N(C=O)C>CCOCC>[CH3:20][O:9][C:8]([C:11]1[CH:12]=[CH:13][C:14]([B:17]([OH:19])[OH:18])=[CH:15][CH:16]=1)=[O:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 167693Trimethylsilyldiazomethane2×HCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 27343694-Methoxycarbonylphenylboronic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of (trimethylsilyl)diazomethane (3 mL, 2 M in hexanes) (Aldrich) was added to a suspension of 4-carboxyphenylboronic acid (1.0 g, 6 mmol) (Lancaster) in ether (50 mL). After stirring for 2 h at room temperature, DMF (8 mL) was added to obtain a clear solution. An additional portion of (trimethylsilyl) diazomethane (3 mL, 2 M in hexanes) was added. After stirring for an additional 2 h, the reaction was quenched by adding acetic acid and concentrating under reduced pressure. Residue was recrystallized from water to give product. (Yield 0.81 9, 75%).

Workup

  1. customto obtain a clear solution
  2. stirringAfter stirring for an additional 2 h
  3. customthe reaction was quenched
  4. additionby adding acetic acid
  5. concentrationconcentrating under reduced pressure
  6. customResidue was recrystallized from water
  7. customto give product
  8. custom(Yield 0.81 9, 75%)

Sources & evidence

ORD record
ord-3e096a92551f433a9c10b4418fd34a1c
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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