Trimethyl borate → HCID 67057756, compound
Reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7](I)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[B:18](OC)([O:21]C)[O:19]C>C1COCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([B:18]([OH:21])[OH:19])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 4-tert-butyl-1-chloro-2-iodobenzene (0.47 g, 1.60 mmol) in dry THF (5 mL) at −78° C., n-butyl lithium (0.76 mL, 1.92 mmol, 2.5 M) was added. The solution was stirred at −78° C. for 30 min. Trimethyl borate (0.53 mL, 4.79 mmol) was added. The solution was stirred at −78° C. for 3 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 3 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-2e03ff4435d444e2810a00a0d6b66753
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07910592B2
Reaction notes
Loading…