Methane → (3-hydroxyphenyl)boronic Acid

HRID 496117노트

반응식

HRID 496117 반응식
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

참가 물질

6

반응물 4

HCID 297MethaneHCID 1118Sulfuric Acid2회HCID 162111393-Aminophenylboronic Acid HemisulfateHCID 23668193Sodium Nitrite

생성물 1

HCID 2734359(3-hydroxyphenyl)boronic Acid수율 94%

시약·촉매·용매 1

HCID 962Water용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d07dcf20e2ac45de86bf1d6b8bf223c5
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06943159B1

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