Methanol → (2,4,6-Trichlorophenyl)methanamine
Reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[C:4]#[N:5].CO.O.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH2:4][NH2:5]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
To a solution of 2,4,6-trichlorobenzonitrile (0.69 mmol) in 2 mL THF was added a solution of BH3 (2.77 mmol, 1M in THF). The reaction mixture was heated to 40° C. for 2 h and then cooled to RT. 1 mL MeOH was added and the mixture was stirred at RT for 30 min. Water was added, the mixture was basified with 1M NaOH solution and extracted twice with EtOAc. The combined organic layers were dried over MgSO4 and concentrated in vacuo to give the desired product as slightly yellow oil.
Workup
- temperaturecooled to RT
- extractionextracted twice with EtOAc
- dry with materialThe combined organic layers were dried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-10168f2bb53847798c2d14ef94c7434c
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409917B2
Reaction notes
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