2-(3-Butoxyphenyl)-2-fluoroacetonitrile → HCID 71152226, compound
Reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH:12]([F:15])[C:13]#[N:14])[CH:9]=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]>C1COCC1>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH:12]([F:15])[CH2:13][NH2:14])[CH:9]=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2-(3-butoxyphenyl)-2-fluoroacetonitrile (109 mg: 0.53 mmol) in dry THF (5 mL), borane tetrahydrofurane complex (2.10 mL; 2.10 mmol) is added and the reaction is stirred at 0° C. for 2 hours and then at RT for 6 hours. An LC/MS shows almost complete conversion. The reaction is quenched adding slowly few drops of EtOH and few drops of conc. HCl/EtOH (1:5) and stirring is continued for 5 min. DCM was then added, followed by 5% aqueous NaHCO3. The two phases are separated and the aqueous phase is extracted twice with DCM. The combined organic layers are dried over Na2SO4, filtered and evaporated. The crude residue is purified using a SCX cartridge (eluant: DCM/MeOH 1/1 to MeOH/conc. aq. NH3 95/5) affording 2-(3-butoxyphenyl)-2-fluoroethanamine (92 mg; 0.43 mmol; 83%) as a pale yellow oil.
Workup
- waitat RT for 6 hours
- customThe reaction is quenched
- additionadding slowly few drops of EtOH and few drops of conc. HCl/EtOH (1:5)
- stirringstirring
- waitis continued for 5 min
- additionDCM was then added
- customThe two phases are separated
- extractionthe aqueous phase is extracted twice with DCM
- dry with materialThe combined organic layers are dried over Na2SO4
- filtrationfiltered
- customevaporated
- customThe crude residue is purified
Sources & evidence
- ORD record
- ord-32d03c35920f43cb80f45eda232504c2
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447029B2
Reaction notes
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