Hexane → (5-(Tert-butyl)-2-((2-methoxyethoxy)methoxy)phenyl)boronic acid
Reaction equation
C([Li])CCC.CCCCCC.Br[C:13]1[CH:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=[CH:15][C:14]=1[O:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29].[B:30](OC)([O:33]C)[O:31]C>O1CCCC1>[C:19]([C:17]1[CH:16]=[CH:15][C:14]([O:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29])=[C:13]([B:30]([OH:33])[OH:31])[CH:18]=1)([CH3:22])([CH3:21])[CH3:20]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
n-Butyllithium in hexane (2.5 M, 4.2 mL, 10.5 mmol) was added dropwise to a solution of give 2-bromo-4-(tert-butyl)-1-((2-methoxyethoxy)methoxy)benzene (3.0 g, 9.46 mmol) and trimethyl borate (1.2 mL, 10.76 mmol) in anhydrous tetrahydrofuran (20 mL) at −78° C. under nitrogen. The reaction mixture was stirred at −78° C. for 20 minutes then at 0° C. for an additional 20 minutes. The reaction was then quenched by the addition of water (20 mL) and the mixture extracted with ether (100 mL). The organic layer was separated, dried (MgSO4), filtered and concentrated under reduced pressure to give (5-(tert-butyl)-2-((2-methoxyethoxy)methoxy)phenyl)boronic acid (2.61 g, 98% yield).
Workup
- waitat 0° C. for an additional 20 minutes
- customThe reaction was then quenched by the addition of water (20 mL)
- extractionthe mixture extracted with ether (100 mL)
- customThe organic layer was separated
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-10aaf23982e64ff9b246c09063ffbe67
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962657B2
Reaction notes
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