Hydrochloric Acid → 3,5-Dichlorophenylboronic acid

HRID 1740284

반응식

HRID 1740284 반응식
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[CH:3]=1.C([O:13][B:14](OC(C)C)[O:15]C(C)C)(C)C.C([Li])CCC.Cl>O1CCCC1.CCCCCC>[Cl:9][C:4]1[CH:3]=[C:2]([B:14]([OH:15])[OH:13])[CH:7]=[C:6]([Cl:8])[CH:5]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 29766Benzene, 1-bromo-3,5-dichloro-HCID 178418339Butyllithium

생성물 1

HCID 27343313,5-Dichlorophenylboronic acid

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

To a cold (-78° C.) solution of 1-bromo-3,5-dichlorobenzene (14 g) and triisopropoxyborane (20.8 ml) in tetrahydrofuran (140 ml) was added dropwise n-butyllithium in hexane (1.66 M, 52.3 ml). The mixture was stirred at -78° C. for one hour and warmed to room temperature over two hours. The reaction mixture was poured onto 2M hydrochloric acid solution (120 ml) and stirred for 10 minutes. The product was extracted with ether (200 ml) 3 times, and the organic layers were combined, washed with brine, dried over magnesium sulfate and evaporated in vacuo. To the residue was added petroleum ether and the crystalline was collected, washed with petroleum ether and dried to give 3,5-dichlorophenyl-dihydroxyborane.

후처리

  1. temperaturewarmed to room temperature over two hours
  2. stirringstirred for 10 minutes
  3. extractionThe product was extracted with ether (200 ml) 3 times
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. additionTo the residue was added petroleum ether
  8. customthe crystalline was collected
  9. washwashed with petroleum ether
  10. customdried

출처 및 근거

ORD 기록
ord-3b868a2f93d7475d853d55e381fe8c10
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05968985

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