Sodium Sulfite → Sodium 2-(4-bromo-phenyl)-ethanesulfonate

HRID 912366Notes

Reaction equation

HRID 912366 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]OS(C)(=O)=O)=[CH:4][CH:3]=1.BrC1C=CC(CCO)=CC=1.CS(Cl)(=O)=O.[O-:30][S:31]([O-:33])=[O:32].[Na+:34].[Na+]>C(O)C.O>[Na+:34].[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][S:31]([O-:33])(=[O:32])=[O:30])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 31297Methanesulfonyl chlorideHCID 728512-(4-Bromophenyl)ethanolHCID 144850904-Bromophenethyl Methanesulfonate

Product 1

HCID 57751107Sodium 2-(4-bromo-phenyl)-ethanesulfonate

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Methanesulfonic acid 2-(4-bromo-phenyl)-ethyl ester (1.39 g) prepared from 2-(4-bromo-phenyl)-ethanol and methanesulfonyl chloride, and Na2SO3 (816 mg) were reacted in ethanol/water (1/1), to obtain a crude product of 2-(4-bromo-phenyl)-ethanesulfonic acid sodium salt as a colorless plate-like crystal. Then, thionyl chloride (3 ml) was left to react in the presence of DMF (500 μl), to obtain 2-(4-bromo-phenyl)-ethanesulfonyl chloride, and further N-methylpiperazine (73 μl) was left to react in dichloromethane (2 ml) in the presence of triethylamine (54 μl), to obtain 1-[2-(4-bromo-phenyl)-ethanesulfonyl]-4-methyl-piperazine as a yellow solid (94 mg, 24%).

Sources & evidence

ORD record
ord-c70ee80a402f422985b6a054a8fe19e3
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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