Bromine → 5-Bromo-2-fluoro-4-hydroxy-benzoic acid methyl ester
Reaction equation
[F:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:13]Br>C(O)(=O)C>[Br:13][C:9]1[C:10]([OH:12])=[CH:11][C:2]([F:1])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 45 °C
Procedure
To a solution of 66.43A (2.03 g, 11.9 mmol) in acetic acid (65 mL) was added a pre-mixed solution of bromine (0.67 mL, 13.1 mmol) in acetic acid (10 mL). The mixture was stirred at 45° C. and monitored with TLC and LC-MS. After 18 hours, the reaction mixture was concentrated under reduced pressure. Brine was added to the residue, and the mixture was extracted three times with EtOAc. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated to provide 66.43B as a white solid (2.12 g, 71% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.13 (1H, d, J=7.4 Hz), 6.82 (1H, d, J=11.3 Hz), 6.04 (1H, s), 3.92 (3H, s).
Workup
- concentrationthe reaction mixture was concentrated under reduced pressure
- additionBrine was added to the residue
- extractionthe mixture was extracted three times with EtOAc
- dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4943c58f006b456fb1196bd72bbd9732
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08030354B2
Reaction notes
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