Reaction equation
Br[C:2]1[CH:7]=[C:6]([CH:8]([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[O:11][CH2:12][CH:13]1[CH2:15][CH2:14]1.[Li]CCCC.C(O[B:25]1[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]1)(C)C>C(OC)CCC>[CH:13]1([CH2:12][O:11][C:3]2[CH:4]=[CH:5][C:6]([CH:8]([F:10])[F:9])=[CH:7][C:2]=2[B:25]2[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]2)[CH2:15][CH2:14]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Bromo-1-cyclopropylmethoxy-4-difluoromethyl-benzene (example B.b18; 24.35 g; 87.9 mmol) is dissolved in dry tert. BuOMe (440 mL). n-BuLi (1.6M in hexane; 60.0 mL; 96.0 mmol) is slowly syringed into the well stirred reaction mixture at −40° C. After one hour commercially available 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (17.86 g; 96.0 mmol) is added at −40° C. followed by stirring at 0° C. for one additional hour. The reaction mixture is quenched by addition of 2M aqueous citric acid (90.0 mL). The organic layer is separated, washed with brine, dried over Mg2SO4 and filtered through a pad of neutral alumina (act.2-3). The solvent is removed under reduced pressure to yield 28.1 g of the title compound as pale yellow oil.
Workup
- customreaction mixture at −40° C
- stirringby stirring at 0° C. for one additional hour
- customThe reaction mixture is quenched by addition of 2M aqueous citric acid (90.0 mL)
- customThe organic layer is separated
- washwashed with brine
- dry with materialdried over Mg2SO4
- filtrationfiltered through a pad of neutral alumina (act.2-3)
- customThe solvent is removed under reduced pressure
Sources & evidence
- ORD record
- ord-7c89ceca2fd849fabc2619d1b5447c09
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376442B2
Linked notes
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