2-bromoheptane

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

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

Procedure: N-Ethyl-N-(1-methylhexyl)aniline was prepared from N-ethylaniline and 2-bromoheptane using the same method as in Example 3i).

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of N-butylaniline (7.45 parts) anhydrous potassium carbonate (7.5 parts), 2-bromoheptane (13.5 parts) and DMF (25 parts) was stirred at 130° C. for 86 hours. The reaction mixture was poured into water, saturated with salt and extracted with ethyl acetate. The organic phase was washed with water, dried (MgSO4) and evaporated to leave N-butyl-N-(1-methylhexyl)aniline (11.8 parts, approximately 60% strength). This material had acetic anhydride (10 parts) added to it prior to further use. extracted with ethyl acetate The organic phase was washed with water dried (MgSO4) evaporated

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 5 g of 6-bromo-2-naphthol, 50 ml of dimethyl sulfoxide, 3.9 ml of 6-bromoheptane, 7.1 g of potassium iodide and 7.1 g of milled potassium carbonate activated at 80° C. in high vacuum is heated to 65° C. for 16 hours. It is then cooled and is partitioned between ethyl acetate and water and the organic phase is washed several times with water, dried over magnesium sulfate, filtered and evaporated down. Chromatography of the residue over 200 g of silica gel using toluene and subsequent crystallization from toluene/hexane (8:1) give 6-bromo-2-heptyloxynaphthalene. activated at 80° C. in high vacuum It is then cooled is partitioned between ethyl acetate and water the organic phase is washed several times with water dried over magnesium sulfate filtered evaporated down toluene and subsequent crystallization from toluene/hexane (8:1)

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of N-butylaniline (7.45 parts) anhydrous potassium carbonate (7.5 parts), 2-bromoheptane (13.5 parts) and DMF (25 parts) was stirred at 130° C. for 86 hours. The reaction mixture was poured into water, saturated with salt and extracted with ethyl acetate. The organic phase was washed with water, dried (MgSO4) and evaporated to leave N-butyl-N-(1-methylhexyl)aniline (11.8 parts, approximately 60% strength). This material had acetic anhydride (10 parts) added to it prior to further use. extracted with ethyl acetate The organic phase was washed with water dried (MgSO4) evaporated

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

Procedure: N-Ethyl-N-(1-methylhexyl)aniline was prepared from N-ethylaniline and 2-bromoheptane using the same method as in Example 3i).

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of N-butylaniline (7.45 parts) anhydrous potassium carbonate (7.5 parts), 2-bromoheptane (13.5 parts) and DMF (25 parts) was stirred at 130° C. for 86 hours. The reaction mixture was poured into water, saturated with salt and extracted with ethyl acetate. The organic phase was washed with water, dried (MgSO4) and evaporated to leave N-butyl-N-(1-methylhexyl)aniline (11.8 parts, approximately 60% strength). This material had acetic anhydride (10 parts) added to it prior to further use. extracted with ethyl acetate The organic phase was washed with water dried (MgSO4) evaporated

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

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

Procedure: N-Ethyl-N-(1-methylhexyl)aniline was prepared from N-ethylaniline and 2-bromoheptane using the same method as in Example 3i).

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

Procedure: N-Ethyl-N-(1-methylhexyl)aniline was prepared from N-ethylaniline and 2-bromoheptane using the same method as in Example 3i).

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of N-butylaniline (7.45 parts) anhydrous potassium carbonate (7.5 parts), 2-bromoheptane (13.5 parts) and DMF (25 parts) was stirred at 130° C. for 86 hours. The reaction mixture was poured into water, saturated with salt and extracted with ethyl acetate. The organic phase was washed with water, dried (MgSO4) and evaporated to leave N-butyl-N-(1-methylhexyl)aniline (11.8 parts, approximately 60% strength). This material had acetic anhydride (10 parts) added to it prior to further use. extracted with ethyl acetate The organic phase was washed with water dried (MgSO4) evaporated

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: p-Bromophenol (295.52 grams (“g”), 1500.00 millimole) is dissolved in anhydrous dimethyl formamide (“DMF”) (500 milliliters) in a 2000 milliliter (“mL”) 3-necked flask equipped with mechanical stirrer and condenser, under an argon atmosphere. To this solution, (1-methyl)hexylbromide (322.38 grams, 1800.00 millimoles), sodium iodide (33.57 g, 225.00 mmol) and anhydrous potassium carbonate (621.95 g, 4500.00 mmol) are added. The resulting suspension is heated to 100° C. and stirred at that temperature for 72 hours. After cooling to room temperature, water (1000 mL) and n-hexane (300 mL) are added. The aqueous layer is separated and extracted with n-hexane (3×100 mL). The combined organic layers are washed with diluted sodium chloride solution (2×100 mL) and dried (MgSO4). The solvent is removed by rotary evaporation under reduced pressure and the residue is filtered using a SiO2 layer (10×10 cm) and n-hexane as eluent. After removal of solvent by rotary evaporation and in vacuo a colorless liquid (245.54 g, 60%) is obtained. equipped with mechanical stirrer and condenser, under an argon atmosphere After cooling to room temperature The aqueous layer is separated extracted with n-hexane (3×100 mL) The combined organic layers are washed with diluted sodium chloride solution (2×100 mL) dried (MgSO4) The solvent is removed by rotary evaporation under reduced pressure the residue is filtered After removal of solvent by rotary evaporation