Sodium Carbonate → Methyl 2-bromo-6-fluorobenzoate
Reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([OH:6])=[O:5].[C:12](=O)([O-])[O-].[Na+].[Na+]>CO.S(=O)(=O)(O)O>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([O:6][CH3:12])=[O:5]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
2-Bromo-6-fluorobenzoic acid (1, 12.50 g, 57 mmol) was dissolved in a mixture of methanol (60 mL) and conc. sulfuric acid (65 mL). The solution was heated to 80° C. and stirred for 12 h. The reaction mixture was cooled and 20% sodium carbonate solution (500 mL) was added slowly to reach pH=8. The mixture was extracted with dichloromethane (3×180 mL), and the combined organic layers were dried over magnesium sulfate and evaporated. The title compound (11.29 g, 48.5 mmol, 85%) was obtained as a brown oil.
Workup
- temperatureThe reaction mixture was cooled
- extractionThe mixture was extracted with dichloromethane (3×180 mL)
- dry with materialthe combined organic layers were dried over magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-73cb7dbecb504f58b9a5a16cbe075a2a
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680099B2
Reaction notes
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