Triisopropyl borate → 2,3-Difluoro-4-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-phenylboronic Acid
Reaction equation
[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]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
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%).
Workup
- stirringThe reaction mixture was stirred at that temperature for 1 h and at room temperature for 10 h
- customquenched with water
- extractionextracted with ethyl acetate
- washwashed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customPurification
- customby recrystallization from hexane
Sources & evidence
- ORD record
- ord-10b1b9bf35734e5bb865fa88f20a46f0
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06703082B1
Reaction notes
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