2-butyl-5-chloro-1-benzofuran

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 2-n-Butyl-5-chlorobenzofuran (9.5 g., 0.046 mol.) was acylated with 8 g. (0.047 mol.) of p-anisoyl chloride as described in the procedure of Example 1 to give 2-n-butyl-5-chloro-3-(4-methoxybenzoyl)benzofuran. Demethylation gives 2-n-butyl-5-chloro-3-(4-hydroxybenzoyl)benzofuran.

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

Procedure: A mixture of 31.5 g. (0.14 mol.) of 2-butyryl-5-chlorobenzofuran and 35 ml. of 98% hydrazine in 70 ml. of diethylene glycol was warmed for a few minutes on a steam bath. Then 23.3 g. of potassium hydroxide was added and the reaction mixture was refluxed for two hours. After cooling, water was added to the mixture and the resulting aqueous solution was extracted with benzene. The extract was washed with water, 10% aqueous hydrochloric acid and water, dried (MgSO4) and concentrated in vacuo to yield 2-n-butyl-5-chlorobenzofuran, b.p. 70°-75° (10-15 mm.). A mixture of 31.5 g the reaction mixture was refluxed for two hours After cooling the resulting aqueous solution was extracted with benzene The extract was washed with water, 10% aqueous hydrochloric acid and water dried (MgSO4) concentrated in vacuo

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

Procedure: 2-n-Butyl-5-chlorobenzofuran (9.5 g., 0.046 mol.) was acylated with 8 g. (0.047 mol.) of anisoyl chloride as described in the procedure of Example 10 to give 2-n-butyl-5-chloro-3-(4'-methoxybenzoyl)benzofuran. Demethylation followed by reaction of the 2-n-butyl-5-chloro-3-(4'-hydroxybenzoyl)benzofuran with epichlorohydrin and subsequent opening of the epoxy compound formed with isopropylamine was carried out as described in the procedures of Examples 9 and 7 to give the title compound.

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

Procedure: A mixture of 31.5 g. (0.14 mol.) of 2-butyryl-5-chlorobenzofuran and 35 ml. of 98% hydrazine in 70 ml. of diethylene glycol was warmed for a few minutes on a steam bath. Then 23.3 g. of potassium hydroxide was added and the reaction mixture was refluxed for two hours. After cooling, water was added to the mixture and the resulting aqueous solution was extracted with benzene. The extract was washed with water, 10% aqueous hydrochloric acid and water, dried (MgSO4) and concentrated in vacuo to yield 2-n-butyl-5-chlorobenzofuran, b.p. 70°-75° (10-15 mm.). A mixture of 31.5 g the reaction mixture was refluxed for two hours After cooling the resulting aqueous solution was extracted with benzene The extract was washed with water, 10% aqueous hydrochloric acid and water dried (MgSO4) concentrated in vacuo