Methanol → HCID 20784721, compound
Reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([F:11])[C:3]=1[C:4]#[N:5].O.CO>C1COCC1>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([F:11])[C:3]=1[CH2:4][NH2:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 2,4-dichloro-6-fluorobenzonitrile (3.87 mmol) in 15 mL THF was added a solution of BH3 (15.5 mmol, 1M in THF) and the mixture was stirred at 60° C. for 1 h. After cooling to 0° C., water was added followed by MeOH and the mixture was then heated to 70° C. for 10 min. The solvent was evaporated, the residue was taken up in water and EtOAc. The aqueous phase was separated, basified with 1M NaOH and it was extracted 3 times with EtOAc. The combined organic layers were dried over MgSO4 and concentrated in vacuo to obtain the desired product as yellow oil.
Workup
- temperatureAfter cooling to 0° C.
- temperaturethe mixture was then heated to 70° C. for 10 min
- customThe solvent was evaporated
- customThe aqueous phase was separated
- extractionwas extracted 3 times with EtOAc
- dry with materialThe combined organic layers were dried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-1dc24c3fa42f47a185e93c7447f3d1d1
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409917B2
Reaction notes
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