Water → Benzenamine, 2-bromo-6-ethynyl-4-(trifluoromethyl)-
Reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([C:12]#[C:13][Si](C)(C)C)[C:3]=1[NH2:18].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([C:12]#[CH:13])[C:3]=1[NH2:18]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
4.26 g of 2-bromo-4-trifluoromethyl-6-trimethylsilanylethynyl-phenylamine (13 mmol) were dissolved in 40 ml THF and the solution was cooled to 0° C. Then 15.2 ml of a 1 M solution of tetrabutylammonium fluoride in THF (15 mmol) were added and the reaction mixture was stirred for 20 min at 0° C. After addition of water, the mixture was extracted with EtOAc and the combined organic extracts were washed with brine, dried with magnesium sulfate, filtered and concentrated. 1.82 g (54%) of 2-bromo-6-ethynyl-4-trifluoromethyl-phenylamine were isolated as a brown solid after purification (silica gel; cyclohexane/EtOAc 9:1). 1H NMR (CDCl3, 300 MHz): δ 3.48 (s, 1H), 5.03 (br s, 2H), 7.54 (s, 1H), 7.65 (s, 1H).
Workup
- extractionthe mixture was extracted with EtOAc
- washthe combined organic extracts were washed with brine
- dry with materialdried with magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-41551fb44a914313a186e6367bf40500
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07259183B2
Reaction notes
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