3-(2,4-Dihydroxyphenyl)-4-(4-methoxyphenyl)-5-methyl-1H-pyrazole → 3-(5-Bromo-2,4-dihydroxyphenyl)-4-(4-methoxyphenyl)-5-methyl-1H-pyrazole
Reaction equation
[Br-:1].[Br-].[Br-].C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.[CH3:37][O:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]2[C:46]([C:51]3[CH:56]=[CH:55][C:54]([OH:57])=[CH:53][C:52]=3[OH:58])=[N:47][NH:48][C:49]=2[CH3:50])=[CH:41][CH:40]=1>ClCCl>[Br:1][C:55]1[CH:56]=[C:51]([C:46]2[C:45]([C:42]3[CH:41]=[CH:40][C:39]([O:38][CH3:37])=[CH:44][CH:43]=3)=[C:49]([CH3:50])[NH:48][N:47]=2)[C:52]([OH:58])=[CH:53][C:54]=1[OH:57]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Benzyltrimethylammonium tribromide (4.0 g, 10.2 mmol) was added portion-wise to a suspension of 4-[4-(4-methoxy-phenyl)-5-methyl-1H-pyrazol-3-yl]-benzene-1,3-diol (2.95 g, 10 mmol) in dichloromethane (50 ml) and the mixture stirred for ˜90 mins. The mixture washed with water (3×50 ml) and saturated aqueous sodium chloride solution (25 ml). The solution was dried over anhydrous magnesium sulphate and concentrated to give a pale yellow solid. Crude product was purified by column chromatography, on silica, eluting with ethyl acetate/hexane (1:2) to give 4-bromo-6-[4-(4-methoxy-phenyl)-5-methyl-1H-pyrazol-3-yl]-benzene-1,3-diol (1.75 g)
Workup
- washThe mixture washed with water (3×50 ml) and saturated aqueous sodium chloride solution (25 ml)
- dry with materialThe solution was dried over anhydrous magnesium sulphate
- concentrationconcentrated
- customto give a pale yellow solid
- customCrude product was purified by column chromatography, on silica
- washeluting with ethyl acetate/hexane (1:2)
Sources & evidence
- ORD record
- ord-ec9372864de248de957d9e9d92820d2b
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07247734B2
Reaction notes
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