反応 #6634

反応方程式

S-(4-bromophenyl) 3,3-dimethyl-thioacrylate

aluminum chloride

Compound 69

S-(4-bromophenyl) 3,3-dimethyl-thioacrylate

→

title compound

4,4-Dimethyl-6-bromo-2-oxo-thiochroman

溶媒

methylene chloride

brine

methylene chloride

反応条件

後処理

1. 1
   温度To a stirred, ice-cooled
2. 2
   workup.ADDITIONwas added under nitrogen
3. 3
   抽出The mixture was extracted with methylene chloride
4. 4
   洗浄the combined organic extracts were washed with saturated NaCl solution
5. 5
   乾燥dried (MgSO4)
6. 6
   その他The solvent was removed in vacuo
7. 7
   その他the residue recrystallized from hexanes

実験手順

To a stirred, ice-cooled suspension of 15.9 g (119 mmol) of aluminum chloride in 140 ml of methylene chloride was added under nitrogen, a solution of 21.64 g (79.9 mmol) of S-(4-bromophenyl) 3,3-dimethyl-thioacrylate (Compound 69) in 100 ml of methylene chloride. The mixture was then stirred at room temperature for 72 h and then poured into 250 g of an ice and brine mixture. The mixture was extracted with methylene chloride and the combined organic extracts were washed with saturated NaCl solution and then dried (MgSO4). The solvent was removed in vacuo and the residue recrystallized from hexanes to give the title compound as white crystals. PMR (CDCl3): δ 1.40 (6H, s), 2.67 (2H, s), 7.31-7.40 (3H, m). MS exact mass, m/e 269.9714 (calcd. for C11H11SOBr, 269.9714).

出典