Carbon Dioxide → 2,3-Difluoro-6-(2-methylallyloxy)benzoic acid
Reaction equation
C([Li])(CC)C.[F:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]([CH3:17])=[CH2:16])=[CH:9][C:8]=1[F:18].[C:19](=[O:21])=[O:20].Cl>C1CCCCC1.O1CCCC1.O>[F:18][C:8]1[C:7]([F:6])=[CH:12][CH:11]=[C:10]([O:13][CH2:14][C:15]([CH3:17])=[CH2:16])[C:9]=1[C:19]([OH:21])=[O:20]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -75 °C
Procedure
To a 1.4 M solution of sec-butyllithium in cyclohexane (6.7 mL) and anhydrous tetrahydrofuran (15 mL) at −75° C. was added 1,2-difluoro-4-(2-methylallyloxy)benzene (731) (1.6 g, 8.68 mmol). The resulting mixture was stirred at −75° C. for 2.5 hours and was then transferred to a round bottom flask containing dry ice. The resulting mixture was shaken for 5 min, and water (10 mL) was added dropwise. The mixture was acidified to pH 1 with concentrated hydrochloric acid and extracted with EtOAc (80 mL×3). The organic phase was washed with brine (60 mL×2), water (60 mL), and dried over anhydrous sodium sulfate, and the solvent removed in vacuo to give an oil 2,3-difluoro-6-(2-methylallyloxy)benzoic acid (732) (1.9 g), The product was used directly in the next step without further purification.
Workup
- customwas then transferred to a round bottom flask
- stirringThe resulting mixture was shaken for 5 min
- extractionextracted with EtOAc (80 mL×3)
- washThe organic phase was washed with brine (60 mL×2), water (60 mL)
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent removed in vacuo
Sources & evidence
- ORD record
- ord-80dc19bc2aa245779f8cb38270a68a92
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08598374B2
Reaction notes
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