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

HRID 1092968Notes

Reaction equation

HRID 1092968 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) is added to a stirred mixture of freshly prepared 2-fluoro-1-methanesulfonyl-4-(2-nitro-propenyl)-benzene (Example 64b) (29 g, 0.112 mol) in THF (50 ml). Water (110 ml) is added and the mixture is heated to 60° C. Concentrated hydrochloric acid (50 ml) is added slowly over 1 h at 60-90° C. The reaction is 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 is washed with water (200 ml) followed by brine (200 ml). After drying (MgSO4) the mixture is absorbed on silica and purified by chromatography, eluting with hexane-ethyl acetate (1:1) to give the title compound.

Workup

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

Sources & evidence

ORD record
ord-7da7ab588b1342a7a6828c021a3aad1e
Source dataset
uspto-grants-2012_03
Patent number
US08129541B2

Reaction notes

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