ethyl 5-chloro-3-phenyl-1H-indole-2-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: All 11 ml (33 g.) of bromine to a mixture of ethyl 5-chloro-3-phenylindole-2-carboxylate (30 g.) in 100 ml of acetic acid at 10- 20°. Stir overnight and then add a solution of sodium bisulfite. Filter and wash the precipitate with water. Stir the solid with methanol and filter to yield the title compound. Recrystallization from methanol yields the analytical sample; m.p. 205°-206°C. Filter wash the precipitate with water Stir the solid with methanol filter

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: All 11 ml (33 g.) of bromine to a mixture of ethyl 5-chloro-3-phenylindole-2-carboxylate (30 g.) in 100 ml of acetic acid at 10- 20°. Stir overnight and then add a solution of sodium bisulfite. Filter and wash the precipitate with water. Stir the solid with methanol and filter to yield the title compound. Recrystallization from methanol yields the analytical sample; m.p. 205°-206°C. Filter wash the precipitate with water Stir the solid with methanol filter

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: All 11 ml (33 g.) of bromine to a mixture of ethyl 5-chloro-3-phenylindole-2-carboxylate (30 g.) in 100 ml of acetic acid at 10- 20°. Stir overnight and then add a solution of sodium bisulfite. Filter and wash the precipitate with water. Stir the solid with methanol and filter to yield the title compound. Recrystallization from methanol yields the analytical sample; m.p. 205°-206°C. Filter wash the precipitate with water Stir the solid with methanol filter

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of sodium hydride (from 7.2 gms., 0.15 mole 50% sodium hydride dispersed in mineral oil) in 125 ml fresh dimethyl formamide (DMF) is added ethyl 3-phenyl-5-chloroindole-2-carboxylate (45 gms, 0.15 mole), as a dry powder, in portions. The reaction is exothermic and requires a water bath to maintain the temperature between 45°-50° C. After stirring 15-20 minutes (at 35° C), chloroacetonitrile (12 grams, 0.15 mole) in 25 ml DMF is added slowly. The temperature rises to 45° C and the mixture is stirred overnight at ambient temperature. The mixture is then transferred to a one liter beaker and 500 ml of ice-water is added slowly. After 15-20 minutes the product is filtered off, washed well with water, and dried on a Buchner funnel. After recrystallization from ethanol the product gives a m.p. of 117°-19° C. There is obtained a total of 46 grams (90.2%), of sufficient purity for the next step. A sample is recrystallized from aqueous ethanol, washed with water and vacuum dried, m.p. 119°-120° C. to maintain the temperature between 45°-50° C is added slowly rises to 45° C is added slowly After 15-20 minutes the product is filtered off washed well with water dried on a Buchner funnel After recrystallization from ethanol the product gives a m.p. of 117°-19° C There is obtained a total of 46 grams (90.2%) A sample is recrystallized from aqueous ethanol washed with water and vacuum dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add 11 ml (33 g.) of bromine to a mixture of ethyl 5-chloro-3-phenylindole-2-carboxylate (30 g.) in 100 ml of acetic acid at 10°-20° . Stir overnight and then add a solution of sodium bisulfite. Filter and wash the precipitate with water. Stir the solid with methanol and filter to yield the title compound. Recrystallization from methanol yields the analytical sample; m.p. 205°-206° C. Filter wash the precipitate with water Stir the solid with methanol filter

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add 11 ml (33 g.) of bromine to a mixture of ethyl 5-chloro-3-phenylindole-2-carboxylate (30 g.) in 100 ml of acetic acid at 10°-20°. Stir overnight and then add a solution of sodium bisulfite. Filter and wash the precipitate with water. Stir the solid with methanol and filter to yield the title compound. Recrystallization from methanol yields the analytical sample; m.p. 205°-206° C. Filter wash the precipitate with water Stir the solid with methanol filter

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: All 11 ml (33 g.) of bromine to a mixture of ethyl 5-chloro-3-phenylindole-2-carboxylate (30 g.) in 100 ml of acetic acid at 10- 20°. Stir overnight and then add a solution of sodium bisulfite. Filter and wash the precipitate with water. Stir the solid with methanol and filter to yield the title compound. Recrystallization from methanol yields the analytical sample; m.p. 205°-206°C. Filter wash the precipitate with water Stir the solid with methanol filter