Hydrochloric Acid → 4-(6-Phenylnaphthalene-2-yl)phenylboronic acid

HRID 1662916노트

반응식

HRID 1662916 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:14]=3)[CH:9]=2)=[CH:4][CH:3]=1.CCCCCC.C([Li])CCC.[B:35](OC(C)C)([O:40]C(C)C)[O:36]C(C)C.Cl>C1(C)C=CC=CC=1.C1COCC1>[C:18]1([C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([B:35]([OH:40])[OH:36])=[CH:3][CH:4]=2)[CH:17]=[CH:16]3)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 21531Triisopropyl borateHCID 575398112-(4-Bromophenyl)-6-phenylnaphthaleneHCID 178418339Butyllithium

생성물 1

HCID 575398474-(6-Phenylnaphthalene-2-yl)phenylboronic acid수율 63%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-60 °C

실험 절차

Under an argon gas atmosphere, a mixture of 15.3 g (42.6 mmol) of 2-(4-bromophenyl)-6-phenylnaphthalene and 200 mL of dehydrated THF was cooled down to −60 degrees C., and added with 32.8 mL (51.1 mmol) of hexane solution of 1.56M n-butyllithium in drops while being stirred. Then, the reaction mixture was stirred for two hours at −60 degrees C. 24.0 g (128 mol) of triisopropyl borate was dropped into the reaction solution at −60 degrees C. Subsequently, the reaction mixture was warmed up to room temperature, and stirred for 17 hours. 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 toluene, so that aqueous phase thereof was eliminated. After organic phase thereof was dried with magnesium sulfate, the solvent was distilled away under reduced pressure. By recrystallizing residue by toluene and hexane, 8.7 g of 4-(6-phenylnaphthalene-2-yl) phenylboronic acid was obtained at an yield of 63%.

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 17 hours
  4. temperatureThe reaction mixture was cooled down to 0 degree C
  5. stirringstirred for one hour at room temperature
  6. customAfter the reaction
  7. dry with materialAfter organic phase thereof was dried with magnesium sulfate
  8. distillationthe solvent was distilled away under reduced pressure
  9. customBy recrystallizing residue by toluene and hexane

출처 및 근거

ORD 기록
ord-f6e07d3117c74c41a6d7e7a2bf104804
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08034256B2

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