Triisopropyl borate → HCID 57423217, compound
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([O:19][B:20](OC(C)C)[O:21]C(C)C)(C)C.C([Li])CCC>C1COCC1>[CH2:12]([O:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([B:20]([OH:21])[OH:19])=[CH:3][CH:4]=1)(=[O:10])=[O:9])[CH:13]([CH3:15])[CH3:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
To a solution of isobutyl 4-bromobenzenesulfonate (56 g, 200 mmol) in 280 ml of THF was added triisopropylborate (84 ml, 1.82 eq) and the reaction mixture was cooled to less than −65° C. To the cooled solution, n-butyllithium (144 ml, 0.9 eq, 1.07 M in hexanes) was slowly added while maintaining the temperature below −65° C. The reaction mixture was stirred for at least 0.5 hours and then was quenched with 1M sulfuric acid (200 ml). The reaction mixture was allowed to warm to ca. 20° C. The layers were separated and the rich organic layer containing 35 g (92% yield) of 4-(isobutoxysulfonyl)phenylboronic acid was used without further purification in the next step.
Workup
- temperaturethe reaction mixture was cooled to less than −65° C
- temperaturewhile maintaining the temperature below −65° C
- customwas quenched with 1M sulfuric acid (200 ml)
- customThe layers were separated
Sources & evidence
- ORD record
- ord-52ffe05b32d84564b4c1e70d557ced82
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415480B2
Reaction notes
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