4-bromo-N-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:; See reaction.notes.procedure_details.

Procedure: 4-Bromo-N-methylaniline (0.7 mL, 5.4 mmol), (4-chlorophenyl)boronic acid (967 mg, 6.2 mmol), Pd(dppf)Cl2 (440 mg, 0.5 mmol), and K2CO3 (1.5 g, 10.8 mmol) were dissolved in 1,4-dioxane (40 mL) and water (10 mL) and the resulting mixture was heated to 80° C. After 16 h the resulting mixture was cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (Na2SO4), and dry packed onto silica gel. Column chromatography yielded the title compound. washed with water and brine dried (Na2SO4) dry

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

Procedure: 3,3-Dimethylacryloyl chloride (3 mL, 27 mmol) was added to a solution of 4-bromo-N-methyl-aniline (4.55 g, 25 mmol) in 150 mL of dichloromethane followed after 5 minutes by triethyl amine (5 mL, 33 mmol). After 2.5 h at ambient temperature, the reaction mixture was washed with water and the organic phase was dried over anhydrous sodium sulfate and evaporated in vacuo to afford the title product as a brown oil in quantitative yield. the reaction mixture was washed with water the organic phase was dried over anhydrous sodium sulfate evaporated in vacuo

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

Procedure: 3,3-Dimethylacryloyl chloride (3 mL, 27 mmol) was added to a solution of 4-bromo-N-methyl-aniline (4.55 g, 25 mmol) in 150 mL of dichloromethane followed after 5 minutes by triethyl amine (5 mL, 33 mmol). After 2.5 h at ambient temperature, the reaction mixture was washed with water and the organic phase was dried over anhydrous sodium sulfate and evaporated in vacuo to afford the title product as a brown oil in quantitative yield. the reaction mixture was washed with water the organic phase was dried over anhydrous sodium sulfate evaporated in vacuo

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

Procedure: 3,3-Dimethylacryloyl chloride (3 mL, 27 mmol) was added to a solution of 4-bromo-N-methyl-aniline (4.55 g, 25 mmol) in 150 mL of dichloromethane followed after 5 minutes by triethyl amine (5 mL, 33 mmol). After 2.5 h at ambient temperature, the reaction mixture was washed with water and the organic phase was dried over anhydrous sodium sulfate and evaporated in vacuo to afford the title product as a brown oil in quantitative yield. the reaction mixture was washed with water the organic phase was dried over anhydrous sodium sulfate evaporated in vacuo

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

Procedure: 3,3-Dimethylacryloyl chloride (3 mL, 27 mmol) was added to a solution of 4-bromo-N-methyl-aniline (4.55 g, 25 mmol) in 150 mL of dichloromethane followed after 5 minutes by triethyl amine (5 mL, 33 mmol). After 2.5 h at ambient temperature, the reaction mixture was washed with water and the organic phase was dried over anhydrous sodium sulfate and evaporated in vacuo to afford the title product as a brown oil in quantitative yield. the reaction mixture was washed with water the organic phase was dried over anhydrous sodium sulfate evaporated in vacuo

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

Procedure: 3,3-Dimethylacryloyl chloride (3 mL, 27 mmol) was added to a solution of 4-bromo-N-methyl-aniline (4.55 g, 25 mmol) in 150 mL of dichloromethane followed after 5 minutes by triethyl amine (5 mL, 33 mmol). After 2.5 h at ambient temperature, the reaction mixture was washed with water and the organic phase was dried over anhydrous sodium sulfate and evaporated in vacuo to afford the title product as a brown oil in quantitative yield. the reaction mixture was washed with water the organic phase was dried over anhydrous sodium sulfate evaporated in vacuo

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

Procedure: 26 g 4-bromo-N-methylaniline (XXI) and 100 ml anhydrous N,N-dimethyl formamide (HCONEt2) were plced into a four-necked flask and cooled down to 0° C. under nitrogen. 40 ml of 2.5 M n-butyl lithium (n-BuLi) solution in n-hexane was dropped with stirring and stirred for 2 hours while maintaining at 0° C. N-hexane and n-butane were evaporated and 16.2 g bromo-cyclohexane was added and stirred under reflux for 8 hours. After cooling, lithium bromide was filtered off and N,N-dimethyl formamide recovered. The residue was recrystallized twice from 95% ethanol to yield 16 g 4bromo-N-methyl-N-cyclohexyl aniline (II). stirred for 2 hours while maintaining at 0° C N-hexane and n-butane were evaporated 16.2 g bromo-cyclohexane was added stirred under reflux for 8 hours After cooling lithium bromide was filtered off N,N-dimethyl formamide recovered The residue was recrystallized twice from 95% ethanol

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

Procedure: 26 g 4-bromo-N-methylaniline (XXI) and 100 ml anhydrous N,N-dimethyl formamide (HCONEt2) were plced into a four-necked flask and cooled down to 0° C. under nitrogen. 40 ml of 2.5 M n-butyl lithium (n-BuLi) solution in n-hexane was dropped with stirring and stirred for 2 hours while maintaining at 0° C. N-hexane and n-butane were evaporated and 16.2 g bromo-cyclohexane was added and stirred under reflux for 8 hours. After cooling, lithium bromide was filtered off and N,N-dimethyl formamide recovered. The residue was recrystallized twice from 95% ethanol to yield 16 g 4bromo-N-methyl-N-cyclohexyl aniline (II). stirred for 2 hours while maintaining at 0° C N-hexane and n-butane were evaporated 16.2 g bromo-cyclohexane was added stirred under reflux for 8 hours After cooling lithium bromide was filtered off N,N-dimethyl formamide recovered The residue was recrystallized twice from 95% ethanol