Hydrochloric Acid → 4-Cyclopropylbenzeneboronic acid

HRID 1038352노트

반응식

HRID 1038352 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[B:11](OC(C)C)([O:16]C(C)C)[O:12]C(C)C.Cl>CCCCCC.C1COCC1.C1(C)C=CC=CC=1>[CH:8]1([C:5]2[CH:6]=[CH:7][C:2]([B:11]([OH:16])[OH:12])=[CH:3][CH:4]=2)[CH2:10][CH2:9]1

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 122213551-Bromo-4-cyclopropylbenzene

생성물 1

HCID 28494284-Cyclopropylbenzeneboronic acid

시약·촉매·용매 3

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

반응 조건

온도
-70 °C

실험 절차

2.5 M nButyllithium in hexane (14.5 mL) is added dropwise to a solution of 1-bromo-4-cyclopropyl-benzene (5.92 g) in THF (14 mL) and toluene (50 mL) chilled to −70° C. The resultant solution is stirred at −70° C. for 30 min before triisopropyl borate (8.5 mL) is added. The solution is warmed to −20° C. and then treated with 4 M aqueous hydrochloric acid (15.5 mL). The reaction mixture is further warmed to room temperature and then the organic phase is separated. The aqueous phase is extracted with ethyl acetate and the combined organic phases are dried (sodium sulphate). The solvent is evaporated and the residue is triturated with a mixture of ether and cyclohexane to give the product as a colorless solid.

후처리

  1. additionis added
  2. temperatureThe solution is warmed to −20° C.
  3. temperatureThe reaction mixture is further warmed to room temperature
  4. customthe organic phase is separated
  5. extractionThe aqueous phase is extracted with ethyl acetate
  6. dry with materialthe combined organic phases are dried (sodium sulphate)
  7. customThe solvent is evaporated
  8. customthe residue is triturated with a mixture of ether and cyclohexane

출처 및 근거

ORD 기록
ord-7ac3731dc04b4cd3bf5682027ab948ca
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08551957B2

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