Hydrochloric Acid → (3-(Phenanthren-9-yl)phenyl)boronic acid

HRID 1660663노트

반응식

HRID 1660663 반응식
Br[C:2]1[CH:3]=[C:4]([C:8]2C3C([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[CH:21]=2)=CC=CC=3)[CH:5]=[CH:6][CH:7]=1.[CH3:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C([Li])CCC.[B:33](OC(C)C)([O:38]C(C)C)[O:34]C(C)C.Cl>ClCCl.C1COCC1>[CH:15]1[C:20]2[CH:21]=[C:8]([C:24]3[CH:23]=[C:22]([B:33]([OH:38])[OH:34])[CH:27]=[CH:26][CH:25]=3)[C:4]3[C:3](=[CH:2][CH:7]=[CH:6][CH:5]=3)[C:19]=2[CH:18]=[CH:17][CH:16]=1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 21531Triisopropyl borateHCID 221380359-(3-Bromophenyl)phenanthreneHCID 178418339Butyllithium

생성물 1

HCID 57539958(3-(Phenanthren-9-yl)phenyl)boronic acid수율 67%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-60 °C

실험 절차

Under an argon gas atmosphere, a mixture of 15.45 g (46.4 mmol) of 9-(3-bromophenyl)phenanthrene and 150 mL of dehydrated THF was cooled down to −60 degrees C., and added with 35.9 mL (55.6 mmol) of hexane solution of 1.55M n-butyllithium in drops while being stirred. Then, the reaction mixture was stirred for two hours at −60 degrees C. The reaction solution was added with 26.2 g (139 mol) of triisopropyl borate in drops at −60 degrees C. Subsequently, the reaction mixture was warmed up to room temperature, and stirred for one hour. Then, the reaction mixture was left for a night. The solvent was distilled away under reduced pressure, such that the reaction mixture was condensed. The reaction mixture was cooled down to 0 degree C. to be further added with solution of hydrochloric acid, and then stirred for one hour at room temperature. After the reaction, the reaction mixture was further added with dichloromethane, so that aqueous phase thereof was eliminated. After organic phase thereof was dried with magnesium sulfate, the solvent was distilled away under reduced pressure. Residue thereof was refined by silica-gel column chromatography, such that 13.4 g of 3-(9-phenanthrenyl)phenylboronic acid was obtained with an yield of 67%.

후처리

  1. stirringThen, the reaction mixture was stirred for two hours at −60 degrees C
  2. temperatureSubsequently, the reaction mixture was warmed up to room temperature
  3. stirringstirred for one hour
  4. waitThen, the reaction mixture was left for a night
  5. distillationThe solvent was distilled away under reduced pressure, such that the reaction mixture
  6. customcondensed
  7. temperatureThe reaction mixture was cooled down to 0 degree C
  8. stirringstirred for one hour at room temperature
  9. customAfter the reaction
  10. dry with materialAfter organic phase thereof was dried with magnesium sulfate
  11. distillationthe solvent was distilled away under reduced pressure
  12. customwas obtained with an yield of 67%

출처 및 근거

ORD 기록
ord-389d1d2bc8424ef189da2da625e704c2
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08029697B2

반응 노트

불러오는 중…