Hydrochloric Acid → Ethanone, 1-[2-methoxy-4-(methylthio)phenyl]-

HRID 39029Notes

Reaction equation

HRID 39029 reaction equation
[CH3:1][S-:2].[Na+].F[C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:13])[CH3:12])=[C:7]([O:14][CH3:15])[CH:6]=1.Cl>CN(C=O)C>[CH3:15][O:14][C:7]1[CH:6]=[C:5]([S:2][CH3:1])[CH:10]=[CH:9][C:8]=1[C:11](=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1428871-(4-Fluoro-2-methoxyphenyl)ethan-1-oneHCID 4378561Sodium methanethiolate

Product 1

HCID 13578023Ethanone, 1-[2-methoxy-4-(methylthio)phenyl]-Yield 108.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium thiomethoxide (1.3 g, 18.5 mmol) in DMF (15 ml) was added to 1-(4-fluoro-2-methoxyphenyl)ethanone (2.85 g, 16.9 mmol) in DMF (5 ml). The mixture was stirred for overnight at room temperature. HCl (1%) was added, the water phase was extracted with EtOAc, the combined organic phases were washed with LiCl (5%), brine and were concentrated to give the title compound (3.6 g) MS m/z (rel. intensity, 70 eV) 196 (M+, 35), 182 (11), 181 (bp), 166 (8), 136 (10).

Workup

  1. extractionthe water phase was extracted with EtOAc
  2. washthe combined organic phases were washed with LiCl (5%), brine
  3. concentrationwere concentrated

Sources & evidence

ORD record
ord-3ef35471bd594085b123d7f59d663396
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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