Hydrochloric Acid → 6-Methoxy-2-naphthaleneboronic acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8](Br)[CH:7]=[CH:6]2.C([Li])CCC.[B:19](OC(C)C)([O:24]C(C)C)[O:20]C(C)C.Cl>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([B:19]([OH:24])[OH:20])[CH:7]=[CH:6]2Participants
Procedure
A solution of 6-methoxy-2-bromonaphthalene (25 g) in tetrahydrofuran (300 ml) was cooled at −78° C. under a nitrogen atmosphere. n-Butyllithium (2.66 M solution in hexane) (42 ml) was added dropwise thereto over 1.5 hours, and the solution was stirred for 30 minutes. Triisopropyl borate (26.5 ml) was added dropwise thereto for 30 minutes, then the solution was stirred for 40 minutes while warming from −78° C. to 0° C. 1N hydrochloric acid (200 ml) and ethyl acetate (200 ml) were sequentially added thereto, the solution was stirred, extracted with ethyl acetate, then washed with brine, dried over anhydrous magnesium sulfate, then the solvent was evaporated in vacuo, the resulting solid was washed with a hexane-diethyl ether system to provide the title compound (18 g).
Workup
- waitfor 30 minutes
- stirringthe solution was stirred for 40 minutes
- temperaturewhile warming from −78° C. to 0° C
- stirringthe solution was stirred
- extractionextracted with ethyl acetate
- washwashed with brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated in vacuo
- washthe resulting solid was washed with a hexane-diethyl ether system
Sources & evidence
- ORD record
- ord-fc827272625d4b56a12faf1cbdada943
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399520B2
Reaction notes
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