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Triisopropyl borate → 2,3-Difluoro-4-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-phenylboronic Acid

HRID 48118
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HRID 48118 반응식
[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([F:26])([F:25])[C:15]([F:24])([F:23])[C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])[CH:5]=[CH:4][C:3]=1I.C([O:31][B:32](OC(C)C)[O:33]C(C)C)(C)C>C1COCC1.C([Li])CCC>[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([F:26])([F:25])[C:15]([F:24])([F:23])[C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])[CH:5]=[CH:4][C:3]=1[B:32]([OH:33])[OH:31]
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참가 물질

5

반응물 2

HCID 21531Triisopropyl borateHCID 206321492,3-Difluoro-1-iodo-4-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-benzene

생성물 1

HCID 112708212,3-Difluoro-4-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-phenylboronic Acid

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 178418339Butyllithium용매

실험 절차

To a solution 2,3-difluoro-1-iodo-4-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-benzene (10A) (1 equi.) in THF (5 mL/mmole), butyllithium (1.3 equi.) was added at −78 C. The reaction mixture was stirred at that temperature for 2 hr,. Then triisopropylborate (1 equi.) was added at that temperature. The reaction mixture was stirred at that temperature for 1 h and at room temperature for 10 h, quenched with water, extracted with ethyl acetate washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by recrystallization from hexane afforded 2,3-difluoro-4-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-phenylboronic acid (11A), as a white solid (75%).

후처리

  1. stirringThe reaction mixture was stirred at that temperature for 1 h and at room temperature for 10 h
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification
  8. customby recrystallization from hexane

출처 및 근거

ORD 기록
ord-10b1b9bf35734e5bb865fa88f20a46f0
출처 데이터셋
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06703082B1

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