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

HRID 6597

반응식

HRID 6597 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

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-88ca5467e26b4c35bf2cc8686a6850bf
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07083832B2

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