Potassium Carbonate → 4-[(3,4-Dichlorobenzyl)oxy]-2,5-difluoro-N-(methylsulfonyl)benzamide
Reaction equation
[F:1][C:2]1[CH:14]=[C:13]([OH:15])[C:12]([F:16])=[CH:11][C:3]=1[C:4]([NH:6][S:7]([CH3:10])(=[O:9])=[O:8])=[O:5].Br[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Cl:26][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=1[Cl:25])[CH2:18][O:15][C:13]1[C:12]([F:16])=[CH:11][C:3]([C:4]([NH:6][S:7]([CH3:10])(=[O:8])=[O:9])=[O:5])=[C:2]([F:1])[CH:14]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2,5-Difluoro-4-hydroxy-N-(methylsulfonyl)benzamide (Preparation 18 10.6 g, 42.2 mmol) in DMSO (53 mL) was added 4-(bromomethyl)-1,2-dichlorobenzene (10.63 g, 44.3 mmol) and potassium carbonate (11.66 g, 84.4 mmol) and the reaction stirred at ambient temperature for 18 hours. The reaction was quenched with aqueous hydrogen chloride solution (1 M, 100 mL) and water (100 mL). The resulting off-white precipitate was stirred at room temperature for 1 hour, filtered and washed with water (3×100 mL). The resulting pale yellow solid was suspended in acetone (106 mL) and heated at reflux for 1 hour. The suspension was then cooled to room temperature and filtered to yield the first crop of the crude title compound as a white solid (11.6 g, 67%).
Workup
- customThe reaction was quenched with aqueous hydrogen chloride solution (1 M, 100 mL) and water (100 mL)
- stirringThe resulting off-white precipitate was stirred at room temperature for 1 hour
- filtrationfiltered
- washwashed with water (3×100 mL)
- temperatureheated
- temperatureat reflux for 1 hour
- temperatureThe suspension was then cooled to room temperature
- filtrationfiltered
Sources & evidence
- ORD record
- ord-35fb45b03b59436ea88df9f1e25f72f3
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096500B2
Reaction notes
Loading…