(2-Amino-5-bromophenyl)(2-fluorophenyl)methanone → 5-Bromo-2-(3,4-dimethoxyphenylsulfonamido)-2'-fluorobenzophenone
Reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[F:12])=[O:5].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([S:28](Cl)(=[O:30])=[O:29])[CH:23]=[CH:24][C:25]=1[O:26][CH3:27]>N1C=CC=CC=1>[Br:17][C:14]1[CH:15]=[CH:16][C:2]([NH:1][S:28]([C:22]2[CH:23]=[CH:24][C:25]([O:26][CH3:27])=[C:20]([O:19][CH3:18])[CH:21]=2)(=[O:30])=[O:29])=[C:3]([CH:13]=1)[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[F:12])=[O:5]Participants
4
Procedure
20 g of 2-amino-5-bromo-2'-fluorobenzophenone are heated at 85° C. for 48 hours in 120 ml of dry pyridine in the presence of 20 g of 3,4-dimethoxyphenylsulfonyl chloride. The mixture is cooled, poured into ice-cold water, the solid is filtered off, the solid is extracted with AcOEt, the organic phase is washed with water, a solution of hydrochloric acid (1N), water and then saline water. After drying over magnesium sulfate and evaporating the solvent under vacuum, a solid is obtained which is recrystallized from DCM/isopropyl ether.
Workup
- temperatureThe mixture is cooled
- additionpoured into ice-cold water
- filtrationthe solid is filtered off
- extractionthe solid is extracted with AcOEt
- washthe organic phase is washed with water
- dry with materialAfter drying over magnesium sulfate
- customevaporating the solvent under vacuum
- customa solid is obtained which
- customis recrystallized from DCM/isopropyl ether
Sources & evidence
- ORD record
- ord-44acd343b15e467caa518c10ed8bfb7f
- Source dataset
- uspto-grants-1995_03
- Patent number
- US05397801
Reaction notes
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