Triisopropyl borate → 2,3-Difluoro4-(4-pentyloxybutoxy)phenylboronic acid

HRID 6597

Reaktionsgleichung

Reaktionsgleichung von HRID 6597
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:3]=1[F:19].C([Li])CCC.C([O:28][B:29](OC(C)C)[O:30]C(C)C)(C)C>C1COCC1>[F:1][C:2]1[C:3]([F:19])=[C:4]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:5]=[CH:6][C:7]=1[B:29]([OH:30])[OH:28]

Komponenten

5

Edukt 3

HCID 21531Triisopropyl borateHCID 220162621,2-Difluoro-3-(4-pentyloxybutoxy)benzeneHCID 178418339Butyllithium

Produkt 1

HCID 220162552,3-Difluoro4-(4-pentyloxybutoxy)phenylboronic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1,2-difluoro-3-(4-pentyloxybutoxy)-benzene (24), (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 gave 2,3-difluoro-4-(4-pentyloxybutoxy)phenylboronic acid (25), as a white solid (75%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-88ca5467e26b4c35bf2cc8686a6850bf
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07083832B2

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