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].BrC1C=C(C(OC)=O)C=C(C=1)C(OC)=O.[CH3:29][NH:30][CH3:31].O1CCCC1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:12][N:30]([CH3:31])[CH3:29])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of methyl 3-bromo-5-formylbenzoate (1.8 g, 7.4 mmol, prepared as described in WO2003/048111 starting from dimethyl 5-bromoisophthalate (Alfa Aesar) in methylene chloride (20 mL) was added a solution of 2.0M dimethylamine in tetrahydrofuran (7.4 mL, 15 mmol) and the reaction was stirred for 15 min. Sodium triacetoxyborohydride (4.7 g, 22 mmol) was then added and the resulting mixture was stirred overnight. Saturated sodium bicarbonate solution was added and the resulting mixture was extracted with ethyl acetate. The organic extract was washed twice with water, once with brine, dried over sodium sulfate, filtered and concentrated to afford product as a light yellow oil (1.87 g, 93%). 1H NMR (400 MHz, CDCl3) δ 8.08-8.03 (m, 1H), 7.90-7.87 (m, 1H), 7.70-7.67 (m, 1H), 3.91 (s, 3H), 3.42 (s, 2H), 2.24 (s, 6H); LCMS (M+H)+: 272.0, 274.0.
Workup
- stirringthe resulting mixture was stirred overnight
- extractionthe resulting mixture was extracted with ethyl acetate
- extractionThe organic extract
- washwas washed twice with water, once with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-b4c2871d2fe64dfab8422307547299cc
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933085B2
Reaction notes
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