Methanol → 2-(Aminomethyl)-3,5-dichlorobenzenemethanol
Reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Cl:13])[C:7]=1[C:14]#[N:15])(=O)C.O.CO>C1COCC1>[NH2:15][CH2:14][C:7]1[C:8]([Cl:13])=[CH:9][C:10]([Cl:12])=[CH:11][C:6]=1[CH2:5][OH:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
To a solution of 3,5-dichloro-2-cyanobenzyl acetate (11.7 mmol) in 50 mL THF was added a solution of BH3 (50 mmol, 1M in THF). The reaction mixture was heated to 75° C. for 7 h and then cooled to 0° C. Water was added followed by MeOH and the mixture was concentrated. The residue was taken up in water and EtOAc, acidified with 1N HCl solution and extracted with DCM. The aqueous phase was then basified with 1M NaOH solution and extracted with DCM. The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification with CC using DCM/Et3N (99/1) to DCM/MeOH/Et3N (90/10/1) gives the desired compound as pinkish solid.
Workup
- temperaturecooled to 0° C
- concentrationthe mixture was concentrated
- extractionextracted with DCM
- extractionextracted with DCM
- dry with materialThe combined organic layers were dried over MgSO4
- concentrationconcentrated in vacuo
- customPurification with CC
Sources & evidence
- ORD record
- ord-edb1037ba85146e69218818efdd5d281
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409917B2
Reaction notes
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