Methane → (3-hydroxyphenyl)boronic Acid

HRID 496117ノート

反応式

HRID 496117 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 2734359(3-hydroxyphenyl)boronic Acid収率 94%

試薬・触媒・溶媒 1

HCID 962Water溶媒3 回

実験手順

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 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.

後処理

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

出典と根拠

ORDレコード
ord-d07dcf20e2ac45de86bf1d6b8bf223c5
出典データセット
uspto-grants-2005_09
特許番号
US06943159B1

反応ノート

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