Dimethylformamide → Methyl 4-((5-chloro-2-fluoro-3-methoxyphenyl)sulfanyl)-3-oxobutanoate

HRID 591456Notes

Reaction equation

HRID 591456 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([F:9])=[C:6]([SH:8])[CH:7]=1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+].Cl[CH2:24][C:25](=[O:31])[CH2:26][C:27]([O:29][CH3:30])=[O:28]>O>[Cl:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([F:9])=[C:6]([S:8][CH2:24][C:25](=[O:31])[CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 36240Methyl 4-chloroacetoacetateHCID 897677705-Chloro-2-fluoro-3-methoxybenzenethiol

Product 1

HCID 89767787Methyl 4-((5-chloro-2-fluoro-3-methoxyphenyl)sulfanyl)-3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 5-chloro-2-fluoro-3-methoxybenzenethiol (303 mg) and DMF (dry) (12 mL) were added K2CO3 (239 mg) and methyl 4-chloro-3-oxobutanoate (0.204 mL) at 0° C. The mixture was stirred at room temperature for 45 min. The mixture was diluted with water and extracted with EtOAc. The combined organic layer was washed successively with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (402 mg).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layer was washed successively with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-bfed6c5e122f4951acc0fe92934f8966
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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