2,3-Dichloropropene → HCID 21875394, compound

HRID 966902Notes

Reaction equation

HRID 966902 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[SH:11].[Cl:12][C:13]([CH2:15]Cl)=[CH2:14].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11][CH2:15][C:13]([Cl:12])=[CH2:14]

Participants

7

Reactant 4

HCID 65652,3-DichloropropeneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 47130122-chloro-5-nitrobenzenethiol

Product 1

HCID 21875394HCID 21875394, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-chloro-5-nitro-benzenethiol (1.0 g, 5.27 mmol, prepared in accordance with the procedure described by Still et al. Synth. Comm. 13, 1181 (1983)) in 15 mL DMF was treated with 2,3-dichloropropene (693 μL, 7.52 mmol) and K2CO3 (433 mg, 3.13 mmol). The mixture was heated at 80° C. for 2 h and then allowed to cool to rt. EtOAc (200 mL) and H2O (100 mL) were added. The organic phase was washed with H2O (2×250 mL), saturated aqueous NaCl (100 mL), dried over MgSO4, and concentrated in vacuo. The crude material was purified by flash column chromatography on silica gel eluting with 20% EtOAc in hexanes to give compound 260A (1.09 g, 89%) as an orange oil.

Workup

  1. temperatureto cool to rt
  2. washThe organic phase was washed with H2O (2×250 mL), saturated aqueous NaCl (100 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash column chromatography on silica gel eluting with 20% EtOAc in hexanes

Sources & evidence

ORD record
ord-1a2035c613624b0e8cd5d0aab9c0e172
Source dataset
uspto-grants-2005_10
Patent number
US06953679B2

Reaction notes

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