反应详情

温度

-78 °C

3-Bromo-N-tert-butoxycarbonyl-N-methylaniline (0.358 g, 1.2 mmol) was dissolved in freshly distilled THF (5 ml) under a N2 atmosphere. The solution was chilled to −78° C. and n-butyl lithium (0.750 ml, 2.0 M solution in cyclohexane, 1.5 mmol) was added. After 15 minutes, sulfuryl chloride (0.121 ml, 1.5 mmol) was added and the reaction was allowed to warm to room temperature and stirring was continued overnight. THF was removed by evaporation and the resulting residue was diluted in EtOAc. Organic phase was washed with H2O and brine before being dried with MgSO4. The solvent was removed in vacuo. Purification by flash chromatography (1:19/EtOAc/Hex gradient to 1:9 and then to 1:4). Recovered 0.089 g (23%) of the product as a colorless oil. Rf=0.14 (1:9 EtOAc/Hex). 1H NMR (CDCl3) 7.96 (1H,s), 7.80 (1H,d), 7.68 (1H,d), 7.57 (1H,t), 3.33 (3H,s), 1.50 (9H,s).

1. temperatureto warm to room temperature
2. waitwas continued overnight
3. customTHF was removed by evaporation
4. additionthe resulting residue was diluted in EtOAc
5. washOrganic phase was washed with H2O and brine
6. dry with materialbefore being dried with MgSO4
7. customThe solvent was removed in vacuo
8. customPurification by flash chromatography (1:19/EtOAc/Hex gradient to 1:9
9. customRecovered 0.089 g (23%) of the product as a colorless oil