3-bromo-4-methylaniline

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:

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:

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

Procedure: Prepared by the method of Example 69a) using 3-bromo-4-methylaniline (2.60 g, Example 78a)), sodium nitrite (1.05 g), concentrated hydrochloric acid (20 ml), anhydrous magnesium chloride (2.6 g), acetic acid saturated with sulfur dioxide (50 ml) and copper (II) chloride (0.37 g). The normal work-up and subsequent treatment with ammonium hydroxide (50 ml) followed by the same work-up afforded the subtitle compound as a solid (1.51 g). Prepared by the method of Example 69a)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium borohydride (30.5 g, 806.2 mmol) was added slowly over 3 hours to a stirring mixture of 3-bromo-4-methylaniline (30 g, 161.2 mmol), ethanol (110 mL), acetic acid (92 mL, 1.6 mol), water (265 mL), acetone (66 mL, 892.2 mmol), and sodium acetate (29.2 g, 214.9 mmol). The solution was stirred at 0° C. for 1 hour. The reaction mixture was poured into the 1:1 mixture of ether and hexane containing 2N KOH. The layers were separated and aqueous layer was extracted with ether/hexane (1:1). The combined organic layers were washed once with water and brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was used directly for the next reaction without further purification: The layers were separated aqueous layer was extracted with ether/hexane (1:1) The combined organic layers were washed once with water and brine dried with MgSO4 filtered concentrated under reduced pressure The residue was used directly for the next reaction without further purification