Acetone → 2-Methylthiophene-3-boronic acid

HRID 1432630Notes

Reaction equation

HRID 1432630 reaction equation
CC1(C)C(C)(C)[O:5][B:4]([C:9]2[CH:13]=[CH:12][S:11][C:10]=2[CH3:14])[O:3]1.CC(C)=O>O>[CH3:14][C:10]1[S:11][CH:12]=[CH:13][C:9]=1[B:4]([OH:5])[OH:3]

Participants

4

Reactant 2

HCID 180AcetoneHCID 455881264,4,5,5-Tetramethyl-2-(2-methylthiophen-3-yl)-1,3,2-dioxaborolane

Product 1

HCID 218846302-Methylthiophene-3-boronic acidYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4,4,5,5-tetramethyl-2-(2-methyl-thiophen-3-yl)-[1,3,2]dioxaborolane (1.52 g, 6.78 mmol), acetone (15 mL) and water (15 mL) is added NaIO4 (2.90 g, 13.56 mmol). The solution is stirred at ambient temperature for 24 hours, then heated to a reflux for 24 hours. The solution is concentrated dissolved in EtOAc (1450 mL), washed with water (100 mL), dried over MgSO4, filtered and concentrated to furnish the title compound (0.75 g, 5.49 mmol, 78%). 1H NMR (CDCl3), δ 2.93 (s, 3H), 7.10 (d, J=5.3 Hz, 1H), 7.51 (d, 5.3 Hz, 1H).

Workup

  1. temperatureheated to
  2. temperaturea reflux for 24 hours
  3. concentrationThe solution is concentrated
  4. dissolutiondissolved in EtOAc (1450 mL)
  5. washwashed with water (100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-55ac376d1b1e43539ef6a69a9c74b65d
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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