Isopropylamine → 2-Isopropylamino-5-(trifluoromethyl)benzoic acid
Reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].C([Li])CCC.F[C:11]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:12]=1[C:13]([OH:15])=[O:14]>C1COCC1>[CH:1]([NH:4][C:11]1[CH:19]=[CH:18][C:17]([C:20]([F:21])([F:23])[F:22])=[CH:16][C:12]=1[C:13]([OH:15])=[O:14])([CH3:3])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Isopropylamine (4.0 mL) was dissolved in THF (20 mL). This solution was cooled to 0° C. and n-butyllithium (2.5 M, 20 mL) was added. The reaction was stirred for 90 min and then transferred to a solution of 2-fluoro-5-(trifluoromethyl)benzoic acid (4.2 g) in THF (40 mL) at-78° C. This mixture was stirred for 15 min and then quenched with aqueous NH4Cl. The mixture was extracted with EtOAc (3×), and the organic layer was dried, filtered, and concentrated in vacuo. Flash chromatography of the resulting residue provided 2-isopropylamino-5-(trifluoromethyl)benzoic acid (2.4 g). MS found: (M+H)+=248.2.
Workup
- custom78° C
- stirringThis mixture was stirred for 15 min
- customquenched with aqueous NH4Cl
- extractionThe mixture was extracted with EtOAc (3×)
- customthe organic layer was dried
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-4d37fab8c1254806a964a5157a1b95bb
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07449493B2
Reaction notes
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