Methane → (3-hydroxyphenyl)boronic Acid

HRID 1767628Notes

Reaction equation

HRID 1767628 reaction equation
S(O)(O)(=O)=O.N[C:7]1[CH:8]=[C:9]([B:13]([OH:15])[OH:14])[CH:10]=[CH:11][CH:12]=1.NC1C=C(B(O)[OH:24])C=CC=1.OS(O)(=O)=O.N([O-])=O.[Na+].C>O>[OH:24][C:7]1[CH:8]=[C:9]([B:13]([OH:15])[OH:14])[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 1118Sulfuric Acid2×HCID 162111393-Aminophenylboronic Acid HemisulfateHCID 23668193Sodium Nitrite

Product 1

HCID 2734359(3-hydroxyphenyl)boronic AcidYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A stirred solution of 3-aminophenylboronic acid hemisulfate (6.2 g; 33.3 mmol) and 50% H2SO4 (3.7 ml; 33.3 mmol) in H2O (100 ml) at −2° C. was added a solution of NaNO2 (2.5 g; 36.3 mmol) in H2O (20 ml) over 1 h. The reaction mixture was slowly added to a stirred solution of conc. H2SO4 (25 ml) in H2O (20 ml) at reflux. After complete addition, the reaction mixture was refluxed for 30 min., cooled, added activated charcoal, heated to reflux, cooled and filtered through celite. The filtrate was saturated with NaCl (s), filtered and extracted with Et2O (5×100 ml). The combined organic fractions were dried (Na2SO4) and evaporated to dryness to give 4.3 g (94%) product.

Workup

  1. temperatureat reflux
  2. additionAfter complete addition
  3. temperaturethe reaction mixture was refluxed for 30 min.
  4. temperaturecooled
  5. additionadded
  6. temperatureheated
  7. temperatureto reflux
  8. temperaturecooled
  9. filtrationfiltered through celite
  10. filtrationfiltered
  11. extractionextracted with Et2O (5×100 ml)
  12. dry with materialThe combined organic fractions were dried (Na2SO4)
  13. customevaporated to dryness

Sources & evidence

ORD record
ord-2f6309304cf54c86a45ebb0b02859f84
Source dataset
uspto-grants-2007_06
Patent number
US07235548B2

Reaction notes

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