Water → 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.C([Li])CCC.[B:23](OC(C)C)([O:28]C(C)C)[O:24]C(C)C.O>C1COCC1.CCCCCCC>[C:14]([Si:11]([CH3:13])([CH3:12])[O:10][CH2:9][CH2:8][C:4]1[CH:3]=[C:2]([B:23]([OH:28])[OH:24])[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 were dissolved in 500 ml of anhydrous THF. 64.6 ml of a 2.7 M solution of n-butyllithium in n-heptane were added dropwise at −70° C. The mixture was stirred for 1 h at −70° C. Then 40.2 ml of triisopropyl borate were added dropwise at −70° C. Stirring was continued for 30 min at −70° C. and the mixture allowed to warm up to −20° C. 500 ml of water were added and the mixture was extracted three time with 500 ml each of DCM. The combined organic layers were dried with magnesium sulfate and evaporated to yield 43.6 g of the title compound.
Workup
- stirringStirring
- waitwas continued for 30 min at −70° C.
- temperatureto warm up to −20° C
- extractionthe mixture was extracted three time with 500 ml each of DCM
- dry with materialThe combined organic layers were dried with magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-d1149202c59f4c48b871c5c4649e2835
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618304B2
Reaction notes
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