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

HRID 6591

Reaction equation

HRID 6591 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-3e1233a3cb904efd828fd79e64ba9c58
Source dataset
uspto-grants-2006_08
Patent number
US07083832B2

Linked notes

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