Hydrochloric Acid → 4-ethoxy-2-trifluoromethylphenylboric Acid
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH3:10])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].C([Li])CCC.CCCCCC.[B:26]([O:35]C(C)C)([O:31]C(C)C)[O:27]C(C)C.Cl>O1CCCC1>[CH2:9]([O:8][C:5]1[CH:6]=[CH:7][C:2]([O:27][B:26]([OH:35])[OH:31])=[C:3]([C:11]([F:14])([F:13])[F:12])[CH:4]=1)[CH3:10]Participants
Conditions
- Temperature
- -78 °C
Procedure
Compound (c) (10.0 g) dissolved in tetrahydrofuran (THF) (40 mL) was cooled to −78° C., a 1.6 M butyllithium/hexane solution (30 mL) was slowly added dropwise and the mixture was stirred at the same temperature for 2 hours. Triisopropyl borate (14.0 g) dissolved in THF (20 mL) was then slowly added dropwise at −78° C., and the mixture was stirred at the same temperature for 1 hour. The temperature was increased to room temperature and the final solution was stirred. After adding 3 M hydrochloric acid (200 mL) dropwise at ice-cooling temperature, the aqueous layer was extracted three times with ether. The organic layers were combined, washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 8.28 g of Compound (d).
Workup
- additionwas then slowly added dropwise at −78° C.
- stirringthe mixture was stirred at the same temperature for 1 hour
- temperatureThe temperature was increased to room temperature
- temperaturecooling temperature
- extractionthe aqueous layer was extracted three times with ether
- washwashed with water
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-5820225fe8974a7692d95ff7a8e72a7a
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07070838B2
Reaction notes
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