Carbon Dioxide → HCID 53755144, compound
Reaction equation
C([N-]C(C)C)(C)C.[Li+].[F:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[C:11]=1[C:12]([O:14][CH3:15])=[O:13].[C:24](=[O:26])=[O:25]>O1CCCC1>[F:9][C:10]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:17]=[CH:18][C:19]=1[C:24]([OH:26])=[O:25]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A solution of lithium diisopropyl amide in dry tetrahydrofuran (prepared from diisopropylamine (17.0 ml) and n-butylithium (48.4 ml) in dry tetrahydrofuran)was added to a solution of methyl 2-fluoro-6-trifluoromethylbenzoate (22.39 g) in dry tetrahydrofuran while maintaining the temperature below -70° C. The mixture was stirred at -78° C. for 3 hours. The solution was poured onto solid carbon dioxide pellets and stirred until it had warmed to room temperature. The mixture was evaporated and treated with hydrochloric acid (2M). It was extracted with ether, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give 2-fluoro-3-methoxycarbonyl-4-trifluoromethylbenzoic acid (24.43 g) as an off-white solid, NMR (CDCl3) 3.95(s,3H), 7.55(d,1H), 8.15(t,1H).
Workup
- temperaturewhile maintaining the temperature below -70° C
- stirringstirred until it
- temperaturehad warmed to room temperature
- customThe mixture was evaporated
- additiontreated with hydrochloric acid (2M)
- extractionIt was extracted with ether
- washwashed with water
- dry with materialdried (MgSO4)
- filtrationfiltered
- customThe filtrate was evaporated to dryness
Sources & evidence
- ORD record
- ord-1b94ff7b21ae435faf261118eb8d221d
- Source dataset
- uspto-grants-1999_01
- Patent number
- US05859283
Reaction notes
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