4-Bromobenzyl bromide → 1-Bromo-4-((methylsulfonyl)methyl)benzene
Reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[CH3:10][S:11]([O-:13])=[O:12].[Na+]>CN(C=O)C.O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][S:11]([CH3:10])(=[O:13])=[O:12])=[CH:4][CH:3]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
A stirred suspension of 4-bromobenzyl bromide (1.0 g, 4.0 mmol) and sodium methanesulfinate (2.04 g, 20 mmol) in DMF (10 mL) is heated 1 h at 60° C. The reaction mixture is then cooled to RT, diluted with water (200 mL) and extracted into EtOAc (3×25 mL). The combined EtOAc phases are washed with water (2×50 mL) and brine (25 mL) then dried (MgSO4) and reduced in vacuo to afford the title compound.
Workup
- temperatureThe reaction mixture is then cooled to RT
- extractionextracted into EtOAc (3×25 mL)
- washThe combined EtOAc phases are washed with water (2×50 mL) and brine (25 mL)
- dry with materialthen dried (MgSO4)
Sources & evidence
- ORD record
- ord-8a5caa5386e04d3da1fb8d05878f75f4
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273747B2
Reaction notes
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