Methanesulfonyl chloride → 1-(2-Chloro-4-methanesulfonamidophenoxy)-2-bromoethane
Reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][Br:9])=[C:4]([Cl:12])[CH:3]=1.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>N1C=CC=CC=1>[Cl:12][C:4]1[CH:3]=[C:2]([NH:1][S:14]([CH3:13])(=[O:16])=[O:15])[CH:11]=[CH:10][C:5]=1[O:6][CH2:7][CH2:8][Br:9]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A portion (2.3 g, 9.18 mmol) of the 1-(4-amino-2-chlorophenoxy)-2-bromoethane produced in (6) above was dissolved in pyridine (10 ml) and the resulting solution was cooled to 0° C., followed by dripping of methanesulfonyl chloride (1.43 ml, 0.018 mol) and stirring at room temperature for 2 h. Thereafter, the solvent was evaporated and the residue was diluted with an aqueous solution of sodium bicarbonate, followed by extraction with chloroform. The extract was dried with sodium sulfate and the solvent was evaporated, with the residue being thereafter purified by being subjected to column chromatography on silica gel using, as an eluent, chloroform containing methanol (6.6%) to yield the end compound 1-(2-chloro-4-methanesulfonamidophenoxy)-2-bromoethane (2.78 g) as a pale yellow solid mass.
Workup
- customThereafter, the solvent was evaporated
- additionthe residue was diluted with an aqueous solution of sodium bicarbonate
- extractionfollowed by extraction with chloroform
- dry with materialThe extract was dried with sodium sulfate
- customthe solvent was evaporated, with the residue
- custombeing thereafter purified
- additionchloroform containing methanol (6.6%)
Sources & evidence
- ORD record
- ord-b678784dda784556972853f6f516468d
- Source dataset
- uspto-grants-2000_05
- Patent number
- US06057358
Reaction notes
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