Trimethyl borate → HCID 57509290, compound
Reaction equation
Br[C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[Cl:11].C([Li])CCC.[B:17](OC)([O:20]C)[O:18]C>C1COCC1>[Cl:11][C:3]1[CH:4]=[CH:5][C:6]([CH:8]([CH3:10])[CH3:9])=[CH:7][C:2]=1[B:17]([OH:20])[OH:18]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 2-bromo-1-chloro-4-isopropylbenzene (0.37 g, 1-59 mmol) in dry THF (5 mL) at −78° C., n-butyl lithium (0.76 mL, 1.90 mmol, 2.5 M) was added. The solution was stirred at −78° C. for 30 min. Trimethyl borate (0.53 mL, 4.76 mmol) was added. The solution was stirred at −78° C. for 2.5 h. The reaction was quenched with saturated aqueous NH4Cl. The aqueous layer was extracted with EtOAc (3×15 mL). The combined EtOAc layers were dried over Na2SO4. The residue was used without further purification after evaporation of the solvent.
Workup
- stirringThe solution was stirred at −78° C. for 2.5 h
- customThe reaction was quenched with saturated aqueous NH4Cl
- extractionThe aqueous layer was extracted with EtOAc (3×15 mL)
- dry with materialThe combined EtOAc layers were dried over Na2SO4
- customThe residue was used without further purification
- customafter evaporation of the solvent
Sources & evidence
- ORD record
- ord-825e77c2745847b698af8325c8d8247c
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07910592B2
Reaction notes
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