Tetrahydrofuran → (3-Nitro-5-(trifluoromethyl)phenyl)methanol
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:7](O)=[O:8])([O-:3])=[O:2].O1CCCC1>CO>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:7][OH:8])[CH:10]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:12]=1)([O-:3])=[O:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
3-Nitro-5-(trifluoromethyl)benzoic acid (5.0 g, 21.2 mmol) was combined with tetrahydrofuran (43 mL) and cooled to 0° C. To this solution was added a 1 M borane tetrahydrofuran complex (42 mL, 42 mmol) cautiously over 15 min and the reaction mixture allowed to warm to room temperature overnight. The mixture was cooled to 0° C., treated with excess methanol and concentrated in vacuo to afford 4.0 g (85%) which was used without further purification. 1H-NMR (CDCl3, 300 MHz) δ 8.39 (s, 1H), 8.35 (s, 1H), 7.94 (s, 1H), 4.87 (s, 2H).
Workup
- additionTo this solution was added a 1 M borane tetrahydrofuran complex (42 mL, 42 mmol) cautiously over 15 min
- temperatureto warm to room temperature overnight
- temperatureThe mixture was cooled to 0° C.
- concentrationconcentrated in vacuo
- customto afford 4.0 g (85%) which
- customwas used without further purification
Sources & evidence
- ORD record
- ord-a785414825394e5d92d3169c8aadbdde
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383821B2
Reaction notes
Loading…