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

HRID 6591

反応式

HRID 6591 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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 h,. 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%).

後処理

  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

出典と根拠

ORDレコード
ord-3e1233a3cb904efd828fd79e64ba9c58
出典データセット
uspto-grants-2006_08
特許番号
US07083832B2

関連ノート

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