Water → 3-(2-Fluoro-4-hydroxyphenyl)-1-methyl-6-trifluoromethyluracil
Reaction equation
B(Br)(Br)Br.[F:5][C:6]1[CH:11]=[C:10]([O:12]C)[CH:9]=[CH:8][C:7]=1[N:14]1[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]([CH3:25])[C:15]1=[O:26].O>C(Cl)Cl>[F:5][C:6]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:7]=1[N:14]1[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:22])([F:23])[F:24])[N:16]([CH3:25])[C:15]1=[O:26]Participants
Procedure
A solution of 32.9 mL (0.033 mole) of boron tribromide (1M in methylene chloride) in 50 mL of methylene chloride was stirred, and a solution of 3.5 grams (0.011 mole) of 3-(2-fluoro-4-methoxyphenyl)-1-methyl-6-trifluoromethyluracil in 50 mL of methylene chloride was added dropwise. Upon completion of addition, the reaction mixture was stirred at ambient temperature for about 18 hours. After this time the reaction mixture was poured into water. The organic layer was separated and the aqueous layer was extracted with methylene chloride. The methylene chloride extract and the organic layer were combined and washed with water. The organic layer was dried with magnesium sulfate and filtered. The filtrate was conc-entrated under reduced pressure, yielding about 2.9 grams of 3-(2-fluoro-4-hydroxyphenyl)-1-methyl-6-trifluoromethyluracil, mp 185°-190° C. The NMR spectrum was consistent with the proposed structure.
Workup
- additionUpon completion of addition
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with methylene chloride
- extractionThe methylene chloride extract
- washwashed with water
- dry with materialThe organic layer was dried with magnesium sulfate
- filtrationfiltered
Sources & evidence
- ORD record
- ord-274b2d2555904e9c93e8890f1c60920c
- Source dataset
- uspto-grants-1995_03
- Patent number
- US05399543
Reaction notes
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