Hydrochloric Acid → 3-Bromo-5-methoxybenzoic acid
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9](Br)[CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:12][O-:13].[Na+].CO.Cl>CN(C)C=O.[Cu]Br>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:13][CH3:12])[CH:10]=1)[C:5]([OH:7])=[O:6]Participants
7
Conditions
- Temperature
- 110 °C
Procedure
A 3-necked flask was charged with 3,5-dibromobenzoic acid (1.0 g, 3.6 mmol), 4 M sodium methoxide solution in methanol (1.2 mL, 4.8 mmol), N,N-dimethylformamide (1.2 mL). The mixture was heated at 110° C. and then copper(I) bromide (51 mg, 0.36 mmol) was added. The mixture was stirred at 110° C. over 4 days. After cooling, the mixture was poured into 1N aq. HCl and adjusted to low pH, extracted with CH2Cl2. The organic layer was dried over Na2SO4, concentrated to dryness. The crude product was used for the next step reaction without further purification. LC-MS: 231.2 [M−1]−.
Workup
- temperatureAfter cooling
- extractionextracted with CH2Cl2
- dry with materialThe organic layer was dried over Na2SO4
- concentrationconcentrated to dryness
- customThe crude product was used for the next step reaction without further purification
Sources & evidence
- ORD record
- ord-8790b059b28848ab87319d3f3e66651f
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946439B2
Reaction notes
Loading…