Tetrahydrofuran → 3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-benzeneboronic Acid
Reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.C1COCC1.C([Li])CCC.C([O:31][B:32](OC(C)C)[O:33]C(C)C)(C)C>CCCCCCC.O>[C:14]([Si:11]([CH3:13])([CH3:12])[O:10][CH2:9][CH2:8][C:4]1[CH:3]=[C:2]([B:32]([OH:33])[OH:31])[CH:7]=[CH:6][CH:5]=1)([CH3:17])([CH3:16])[CH3:15]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -70 °C
Procedure
50.0 g of [2-(3-Bromo-phenyl)-ethoxy]-tert-butyl-dimethyl-silane was dissolved using 500 ml of anhydrous THF and 64.6 ml of a 2.7M solution of n-butyllithium in n-heptane added dropwise at −70° C. The reaction mixture was then stirred at −70° C. for 1 h. 40.2 ml of triisopropylborate was then added dropwise at −70° C. and stirring was continued for 30 minutes at −70° C. The mixture was then allowed to warm to −20° C. and 500 ml of water added. The reaction mixture was then allowed to warm to room temperature and extracted three times using 300 ml of CH2Cl2 each. The organic layer was then dried using MgSO4 and evaporated to yield 43.6 g of the title compound, used without further purification.
Workup
- additionadded dropwise at −70° C
- stirringstirring
- waitwas continued for 30 minutes at −70° C
- temperatureto warm to −20° C.
- temperatureto warm to room temperature
- extractionextracted three times
- customThe organic layer was then dried
- customevaporated
Sources & evidence
- ORD record
- ord-a30b4bdf301c4ec38f699ae65e041a7a
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018383B2
Reaction notes
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