Potassium Phosphate, Tribasic → 3-(4-Methanesulfonyl-phenoxy)-5-methoxymethoxy-benzoic acid methyl ester
Reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:41][O:42][C:43](=[O:55])[C:44]1[CH:49]=[C:48]([OH:50])[CH:47]=[C:46]([O:51][CH2:52][O:53][CH3:54])[CH:45]=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OC(=O)C)C>[CH3:41][O:42][C:43](=[O:55])[C:44]1[CH:45]=[C:46]([O:51][CH2:52][O:53][CH3:54])[CH:47]=[C:48]([O:50][C:8]2[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=2)[CH:49]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 130 °C
Procedure
After adding 33.4 g (142 mmol) of 4-methanesulfonyl-bromobenzene, 2.67 g (11.9 mmol) of palladium acetate, 5.31 g (17.8 mmol) of 2-(di-tert-butylphosphino)biphenyl and 50.3 g (237 mmol) of potassium phosphate to a solution of 25.0 g (119 mmol) of 5-hydroxy-3-methoxymethoxybenzoic acid methyl ester in toluene (375 ml), the reactor was sealed and the mixture was subsequently stirred at 130° C. for 6 hours. Acetic acid ethyl ester was added to the reaction mixture, which was then filtered and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=2:1) to obtain 31.0 g of 3-(4-methanesulfonyl-phenoxy)-5-methoxymethoxy-benzoic acid methyl ester (yield: 69%) as a white solid.
Workup
- customthe reactor was sealed
- filtrationwas then filtered
- concentrationconcentrated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=2:1)
Sources & evidence
- ORD record
- ord-8dbd8fa8486c47e6a4f2277da2e4f1a7
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07754743B2
Reaction notes
Loading…