반응 #676841

반응 방정식

2-chlorothiophenol

chloroacetone

K2CO3

→

title compound

수율 64.0%

7-Chloro-3-methylbenzothiophene

수율 64.0%

용매

acetone

반응 조건

후처리

1. 1
   온도was refluxed for 2 h
2. 2
   여과The mixture was filtered
3. 3
   기타the solvent evaporated
4. 4
   workup.DISSOLUTIONThe crude product was dissolved in chlorobenzene (30 mL)
5. 5
   workup.ADDITIONpolyphosphoric acid (PPA, 0.5 g) was added
6. 6
   온도The resulting mixture was refluxed over night (Plé et al., (1988) J. Heterocyclic Chem. 25, 1271-1272)
7. 7
   workup.ADDITIONAdditional PPA (0.5 g) was added
8. 8
   온도the reaction mixture was refluxed for another 7 h
9. 9
   기타The solvent was decanted from the PPA-residue
10. 10
    workup.ADDITIONthe residue was treated with CH2Cl2
11. 11
    세척the combined organic extracts were washed with water
12. 12
    기타dried
13. 13
    기타the solvents were removed by evaporation
14. 14
    기타The crude product was purified on silica

실험 절차

A mixture of 2-chlorothiophenol (750 μL, 6.6 mmol), chloroacetone (1.1 mL, 13.8 mmol) and K2CO3 (1.8 g, 13 mmol) in acetone (15 mL) was refluxed for 2 h. The mixture was filtered and the solvent evaporated. The crude product was dissolved in chlorobenzene (30 mL) and polyphosphoric acid (PPA, 0.5 g) was added. The resulting mixture was refluxed over night (Plé et al., (1988) J. Heterocyclic Chem. 25, 1271-1272). Additional PPA (0.5 g) was added and the reaction mixture was refluxed for another 7 h. The solvent was decanted from the PPA-residue, the residue was treated with CH2Cl2 and the combined organic extracts were washed with water and dried, and then the solvents were removed by evaporation. The crude product was purified on silica using heptane as eluent, to give the title compound (770 mg, 64% over two steps). 1H NMR (400 MHz, CDCl3) δ ppm 2.44 (d, J=1.20 Hz, 3 H) 7.14 (q, J=1.20 Hz, 1 H) 7.32-7.38 (m, 2 H) 7.60-7.65 (m, 1 H)

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