반응 #160174

반응 방정식

Potassium carbonate

methyl 4-sulfanylbenzoate

1-bromo-2-methyl-propane

→

methyl 4-isobutylsulfanylbenzoate

수율 83.0%

용매

DMF

반응 조건

후처리

1. 1
   기타the resulting solid was removed by filtration
2. 2
   기타The filtrate were partitioned between ethyl acetate (100 mL) and water (100 mL)
3. 3
   기타The layers were separated
4. 4
   세척the organic layer was washed with brine solution
5. 5
   건조dried over sodium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated in vacuo

실험 절차

Potassium carbonate (1.2 g, 8.9 mmol) was added to a mixture of methyl 4-sulfanylbenzoate (1.0 g, 6.0 mmol), 1-bromo-2-methyl-propane (1.2 g, 970 μL, 8.9 mmol), and DMF (10 mL) at room temperature. The reaction mixture was allowed to stir for 4 hours and the resulting solid was removed by filtration. The filtrate were partitioned between ethyl acetate (100 mL) and water (100 mL). The layers were separated and the organic layer was washed with brine solution, then dried over sodium sulfate, filtered and concentrated in vacuo to give methyl 4-isobutylsulfanylbenzoate (1.1 g, 83%) as a clear oil. ESI-MS m/z calc. 242.0. Found 243.2 (M+1)+; Retention time: 1.73 minutes (3 min run). 1H NMR (400 MHz, CDCl3) δ 8.30 (d, J=8.3 Hz, 2H), 8.05 (d, J=8.3 Hz, 2H), 3.03 (d, J=6.5 Hz, 2H), 2.27 (dt, J=13.3, 6.6 Hz, 1H), 1.08 (d, J=6.7 Hz, 6H).

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