Ammonium formate → 2-(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)ethanamine
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][N+:17]([O-])=O)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:20]([F:23])([F:22])[F:21].C([O-])=O.[NH4+]>CO.O.[Zn]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH2:17])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:20]([F:21])([F:22])[F:23]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 1-chloro-4-(4-(2-nitroethyl)phenoxy)-2-(trifluoromethyl)benzene (21 g, 60.7 mmol) and ammonium formate (30.6 g, 486 mmol) in methanol (250 mL) and water (250 mL), was added zinc powder (15.89 g, 243 mmol). The reaction mixture was stirred at 80° C. for 2 h, filtered through a glass grit and washed with methanol. The filtrate was concentrated and the residue was extracted with DCM (200 mL), and then washed with sat. NaHCO3 (100 mL), brine, and dried over anhydrous Na2SO4 and concentrated. Purification via FC (DCM/CH3OH=100/8) afforded the title compound (7.0 g) as a yellow oil.
Workup
- filtrationfiltered through a glass grit
- washwashed with methanol
- concentrationThe filtrate was concentrated
- extractionthe residue was extracted with DCM (200 mL)
- washwashed with sat. NaHCO3 (100 mL), brine
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated
- customPurification via FC (DCM/CH3OH=100/8)
Sources & evidence
- ORD record
- ord-66714892334d4d1e838afa23e3f840d3
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09273054B2
Reaction notes
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