Dimethylamine → Methyl 3-bromo-5-((dimethylamino)methyl)benzoate
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH:12]=O)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:14][NH:15][CH3:16].C1COCC1.C([BH3-])#N.[Na+]>O.[Cl-].[Cl-].[Zn+2].CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:12][N:15]([CH3:16])[CH3:14])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
A mixture of methyl 3-bromo-5-formylbenzoate (200 mg, 0.82 mmol), methanol (3 mL), 2.0 M dimethylamine solution in THF (0.3 mL, 6 mmol), zinc dichloride (30 mg, 0.22 mmol), and sodium cyanoborohydride (200 mg, 3.2 mmol) was stirred at 0° C. for 1 h. The mixture was diluted with water (10 mL) and the aqueous layer was extracted with EtOAc (15 mL×3). The combined organic layers were dried over anhydrous MgSO4 and concentrated. The residue was purified by silica gel chromatography to afford the title compound.
Workup
- extractionthe aqueous layer was extracted with EtOAc (15 mL×3)
- dry with materialThe combined organic layers were dried over anhydrous MgSO4
- concentrationconcentrated
- customThe residue was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-4a97d3ccf2bb4cebb2125f3d7ef959f8
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946439B2
Reaction notes
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