反应详情

温度

2.5 °C

5-Amino-1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran (18 g, 0.06 mole) is dissolved in water (100 ml) and H2SO4(8 ml). NaNO2(4.1 g, 0.06 mole) is dissolved in water (20 ml) and added dropwise below 5° C. The diazotised solution is stirred for 0.5 hour at 0-5° C. pH is brought to 6.5 by adding a saturated solution of Na2CO3. This solution is added to a mixture of water (100 ml) and toluene (120 ml) containing CuCN(6 g, 0.067 mole) and NaCN (10 g, 0.2 mole) at 50-60C°. Stirring is continued for 0.5 hour. The phases are separated and the aqueous phase is further extracted with toluene (100 ml). The combined organic phase is washed with NaCN(10% aq., 2×50 ml). The solvent is removed in vacuo and the residue is chromatograhed on silica gel (ethyl acetate: n-heptane: triethylamine; 85:10:5 ) to give the title compound (6 g, 32%) as an oil.

1. additionadded dropwise below 5° C
2. stirringStirring
3. waitis continued for 0.5 hour
4. customThe phases are separated
5. extractionthe aqueous phase is further extracted with toluene (100 ml)
6. washThe combined organic phase is washed with NaCN(10% aq., 2×50 ml)
7. customThe solvent is removed in vacuo