Diethyl Ether → 2-Chloro-4-(methoxycarbonyl)benzeneboronic acid

HRID 452645Notes

Reaction equation

HRID 452645 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[B:11]([OH:13])[OH:12])[C:5]([OH:7])=[O:6].[CH3:14]N(C)C=O.C(OCC)C.C[Si](N=[N+]=[N-])(C)C.CCCCCC>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]([O:7][CH3:14])=[O:6])[CH:8]=[CH:9][C:10]=1[B:11]([OH:13])[OH:12]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 17750227SimtuzumabHCID 86640031Trimethylsilylazide hexane

Product 1

HCID 221712912-Chloro-4-(methoxycarbonyl)benzeneboronic acidYield 42%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 3-chloro-4-(dihydroxyboryl)benzoic acid (1.00 g, 5.10 mmol), N,N-dimethylformamide (10 mL) and diethyl ether (1 ml) was added dropwise a 0.6 M trimethylsilylazide-hexane solution (10.2 mL, 6.12 mmol), and the resulting mixture was stirred overnight at room temperature. Acetic acid was added to the reaction mixture, and the mixture was concentrated under reduced pressure. Water was added to the residue, and the precipitate was collected by filtration and recrystallized from water to give the title compound (0.46 g, yield 42%) as colorless crystals.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionWater was added to the residue
  3. filtrationthe precipitate was collected by filtration
  4. customrecrystallized from water

Sources & evidence

ORD record
ord-5c8c2d12884f4a1daa2ad21638087b33
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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