1-Fluoro-4-(methylsulphonyl)benzene → 3814-25-3

HRID 1374795Notes

Reaction equation

HRID 1374795 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.O.[SH-:13].[Na+]>CN(C=O)C>[CH3:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([SH:13])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 679941-Fluoro-4-(methylsulphonyl)benzeneHCID 16211346Sodium hydrosulfide hydrate

Product 1

HCID 134103233814-25-3Yield 105.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Fluoro-4-(methylsulfonyl)-benzene (1.74 g) and sodium hydrosulphide hydrate (0.67 g) were dissolved in DMF (10 ml) and stirred at room temperature for 24 hours. The reaction was quenched with water, acidified with 2M hydrochloric acid (20 ml) and extracted with ethyl acetate (2×50 ml). The combined extracts were then washed with water (2×25 ml) and brine (20 ml). The organic solution was dried (MgSO4), filtered and evaporated in vacuo to yield the sub-title compound as a white solid (1.8 g).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate (2×50 ml)
  3. washThe combined extracts were then washed with water (2×25 ml) and brine (20 ml)
  4. dry with materialThe organic solution was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-8240b43896094983becf263f15b42d2b
Source dataset
uspto-grants-2007_01
Patent number
US07166607B2

Reaction notes

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