Diethylamine → Methyl 3-bromo-5-(1-(diethylamino)-2-hydroxyethyl)benzoate
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH:12]2[CH2:14][O:13]2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH2:15]([NH:17][CH2:18][CH3:19])[CH3:16]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH:12]([N:17]([CH2:18][CH3:19])[CH2:15][CH3:16])[CH2:14][OH:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Into a 20 mL reaction vessel were combined methyl 3-bromo-5-(oxiran-2-yl)benzoate (0.10 g, 0.39 mmol), ethanol (10 mL), and diethylamine (120 μL, 1.2 mmol). The mixture was heated at 50° C. overnight, and then concentrated. The residue was purified by preparative HPLC (100×21.2 mm C18 column, CH3CN/water[10 mM Et2NH]) to afford the title compound.
Workup
- customInto a 20 mL reaction vessel
- concentrationconcentrated
- customThe residue was purified by preparative HPLC (100×21.2 mm C18 column, CH3CN/water[10 mM Et2NH])
Sources & evidence
- ORD record
- ord-65dbc434fc1548c68fbc74d0bdee725c
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946439B2
Reaction notes
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