Water → p-Fluorophenylmethylsulfone

HRID 1492363Notes

Reaction equation

HRID 1492363 reaction equation
[S:1](S([O-])=O)([O-:3])=[O:2].[Na+].[Na+].[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Cl)=[CH:12][CH:11]=1.O>CN(C=O)C>[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][S:1]([CH2:14][C:13]2[CH:16]=[CH:17][C:10]([F:9])=[CH:11][CH:12]=2)(=[O:3])=[O:2])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 96024-Fluorobenzyl chlorideHCID 24489Sodium Dithionite

Product 1

HCID 11989600p-FluorophenylmethylsulfoneYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a well-stirred suspension of 6.95 grams (40 mmol) of sodium hydrosulfite in 100 ml DMF was added 5.10 grams (35.3 mmol) of 4-fluoro benzyl chloride. The mixture was stirred at room temperature for five hours, then brought to 85° C. for 20 hours. The warm mixture was poured into 400 ml ice, and the total volume brought to 700 ml with water. The solid precipitates were isolated to give 2.3 grams (8.1 mmol; 46% yield) of bis(4-fluoro benzyl) sulfone. Recrystallization from toluene gave the pure compound as white needles (top 193° C.).

Workup

  1. waitbrought to 85° C. for 20 hours
  2. customThe solid precipitates
  3. customwere isolated

Sources & evidence

ORD record
ord-e807e083b13b4fe78a8d08a3f9aaf03d
Source dataset
uspto-grants-1994_12
Patent number
US05374504

Reaction notes

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