Phenol → 4-(3-(N-methylsulfamoyl)phenyloxy)benzene
Reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[CH3:14][NH:15][S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21](Br)[CH:20]=1)(=[O:18])=[O:17]>CN(C=O)C.[Cu]I>[CH3:14][NH:15][S:16]([C:19]1[CH:20]=[C:21]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:22]=[CH:23][CH:24]=1)(=[O:18])=[O:17]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a slurry of phenol (1.9 g, 20 mmol), K2CO3 (6.0 g, 40 mmol), and CuI (4 g, 20 mmol) in DMF (25 mL) was added N-methyl-3-bromobenzenesulfonamide (2.5 g, 10 mmol), and the resulting mixture was stirred at the reflux temp. overnight, cooled to room temp., and separated between EtOAc (50 mL) and a 1 N HCl solution (50 mL). The aqueous layer was back-extracted with EtOAc (2×50 mL). The combined organic phases were sequentially washed with water (2×50 mL) and a saturated NaCl solution (50 mL), dried (MgSO4), and concentrated under reduced pressure. The residual oil was purified by column chromatography (30% EtOAc/70% hexane) to give 4-(3-(N-methylsulfamoyl)phenyloxy)benzene (0.30 g).
Workup
- temperatureovernight, cooled to room temp.
- customseparated between EtOAc (50 mL)
- extractionThe aqueous layer was back-extracted with EtOAc (2×50 mL)
- washThe combined organic phases were sequentially washed with water (2×50 mL)
- dry with materiala saturated NaCl solution (50 mL), dried (MgSO4)
- concentrationconcentrated under reduced pressure
- customThe residual oil was purified by column chromatography (30% EtOAc/70% hexane)
Sources & evidence
- ORD record
- ord-06ae73dc4a0c43308c9126c1333fa8b9
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08841330B2
Reaction notes
Loading…