Hydrochloric Acid → 1-(3-Fluoro-4-(methylsulfonyl)phenyl)propan-2-one

HRID 1672508Notes

Reaction equation

HRID 1672508 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]=[C:9]([N+]([O-])=O)[CH3:10])[CH:5]=[CH:4][C:3]=1[S:14]([CH3:17])(=[O:16])=[O:15].Cl.C1C[O:22]CC1>O.[Fe]>[F:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9](=[O:22])[CH3:10])[CH:5]=[CH:4][C:3]=1[S:14]([CH3:17])(=[O:16])=[O:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 665884842-Fluoro-1-methanesulfonyl-4-(2-nitro-propenyl)-benzene

Product 1

HCID 573512781-(3-Fluoro-4-(methylsulfonyl)phenyl)propan-2-one

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

Iron powder (25 g, 0.45 mol) was added to a stirred mixture of freshly prepared 2-fluoro-1-methanesulfonyl-4-(2-nitro-propenyl)-benzene (Example AA2) (29 g, 0.112 mol) in THF (50 ml). Water (110 ml) was added and the mixture is heated to 60° C. Concentrated hydrochloric acid (50 ml) was added slowly over 1 h at 60-90° C. The reaction was then stirred at 100° C. for 20 hours then diluted with cold water (500 ml) and filtered through Celite™ filter material washing with chloroform (500 ml). The organic extract was washed with water (200 ml) followed by brine (200 ml). After drying (MgSO4) the mixture was absorbed on silica and purified by chromatography, eluting with hexane-ethyl acetate (1:1) to give the titled compound.

Workup

  1. filtrationfiltered through Celite™
  2. filtrationfilter material
  3. washwashing with chloroform (500 ml)
  4. extractionThe organic extract
  5. washwas washed with water (200 ml)
  6. dry with materialAfter drying (MgSO4) the mixture
  7. customwas absorbed on silica
  8. custompurified by chromatography
  9. washeluting with hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-9a07a0dccb1b42d3bde9ea609449b97d
Source dataset
uspto-grants-2011_08
Patent number
US07998990B2

Reaction notes

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