methyl 2-bromohexanoate

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: 3.5 g of 2-hydroxy-4,6-dimethoxypyrimidine, 4.7 g of methyl 2-bromohexanoate, 50 ml of N,N-dimethylformamide and 3.3 g of anhydrous potassium carbonate were stirred at a temperature of from 85° to 90° C. for 3 hours. The reaction mixture was cooled to room temperature and then diluted with water. This aqueous mixture was extracted with ethyl ether. The ethyl ether extract was washed with water and dried. Then, ethyl ether was removed by distillation under reduced pressure to obtain a slightly yellow oily substance. The slightly yellow oily substance was purified by silica gel column chromatography (eluent: hexane/ethyl acetate =6/1) to obtain 4.7 g of the desired product. This aqueous mixture was extracted with ethyl ether The ethyl ether extract was washed with water dried Then, ethyl ether was removed by distillation under reduced pressure to obtain a slightly yellow oily substance The slightly yellow oily substance was purified by silica gel column chromatography (eluent: hexane/ethyl acetate =6/1)

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

Procedure: To a solution of 2-bromo-hexanoic acid methyl ester (0.500 g, 2.404 mmol) and 4-fluoro-3-methylaniline (0.301 g, 2.404 mmol) in 15 mL of DMF, was added K2CO3 (1.661 g, 12.020 mmol). After stirring at room temperature under N2 for 88 h, the reaction mixture was diluted with 60 mL of water and extracted with dichloromethane (60 mL×3). The organic extracts were combined dried over anhydrous Na2SO4 and the solvent removed under reduced pressure. Flash chromatography (silica gel) eluting with 0-20% ethyl acetate/hexanes afforded the title compound as brown oil (0.273 g, 45% yield). LC-MS: tR=9.9 min; m/z 254 (M+H)+. extracted with dichloromethane (60 mL×3) The organic extracts were combined dried over anhydrous Na2SO4 the solvent removed under reduced pressure Flash chromatography (silica gel) eluting with 0-20% ethyl acetate/hexanes

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

Procedure: 0.3 moles of 6 bromohexanoyl chloride are dissolved in 150 ml of benzene. 26 g (0.34 moles) of methanol are added, applying cooling, and then 45 g (0.445 moles) of triethylamine in solution in 50 ml of benzene are added drop by drop. The mixture is agitated at ambient temperature for 16 hours. The reaction medium is then poured into water, acidified with HCl. The benzene is extracted. The raw product is then distilled under vacuum. This gives 43.7 g of ester with a boiling point of approx. 80° C. at a pressure of 2.25.10-2Pa of mercury; the yield is 69.7 percent. applying cooling The benzene is extracted The raw product is then distilled under vacuum

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

Procedure: 0.3 moles of 6 bromohexanoyl chloride are dissolved in 150 ml of benzene. 26 g (0.34 moles) of methanol are added, applying cooling, and then 45 g (0.445 moles) of triethylamine in solution in 50 ml of benzene are added drop by drop. The mixture is agitated at ambient temperature for 16 hours. The reaction medium is then poured into water, acidified with HCl. The benzene is extracted. The raw product is then distilled under vacuum. This gives 43.7 g of ester with a boiling point of approx. 80° C. at a pressure of 2.25.10-2Pa of mercury; the yield is 69.7 percent. applying cooling The benzene is extracted The raw product is then distilled under vacuum

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

Procedure: 14.63 grams of 2-bromohexanoic acid methyl ester, 8.52 grams of potassium cyanate and 7.85 grams of methanol were heated in 70 ml of dimethylformamide (DMF) at 100° C. for 45 minutes under vigorous stirring. After the cooling off of the reaction mixture the salts were filtered off and the filtrate concentrated in a vacuum. The viscous residue was taken up with 50 ml of acetone and the undissolved material filtered off. Subsequently the acetone was distilled off and the residue fractionated in the high vacuum. There resulted 10.75 grams (75.5%) of 2-methoxycarbonylaminohexanoic acid methyl ester having a boiling point of 78° C./0.007 mbar. After the cooling off of the reaction mixture the salts were filtered off the filtrate concentrated in a vacuum the undissolved material filtered off Subsequently the acetone was distilled off

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

Procedure: 14.63 grams of 2-bromohexanoic acid methyl ester, 8.52 grams of potassium cyanate and 7.85 grams of methanol were heated in 70 ml of dimethylformamide (DMF) at 100° C. for 45 minutes under vigorous stirring. After the cooling off of the reaction mixture the salts were filtered off and the filtrate concentrated in a vacuum. The viscous residue was taken up with 50 ml of acetone and the undissolved material filtered off. Subsequently the acetone was distilled off and the residue fractionated in the high vacuum. There resulted 10.75 grams (75.5%) of 2-methoxycarbonylaminohexanoic acid methyl ester having a boiling point of 78° C./0.007 mbar. After the cooling off of the reaction mixture the salts were filtered off the filtrate concentrated in a vacuum the undissolved material filtered off Subsequently the acetone was distilled off

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

Procedure: 15.2 g of methyl salicylate and 18.0 g of potassium carbonate were introduced into 125 ml of acetonitrile in a 250 ml flask under an argon atmosphere and, at room temperature, 20.9 g of methyl 2-bromohexanoate were added. The colourless suspension was heated under reflux with stirring for 16 hours, and the progress of the reaction was checked by thin-layer chromatography. After cooling to room temperature, the suspension was filtered and the residue was washed with acetone. Concentration of the filtrate in vacuo resulted in 27.8 g (99% of theory) of methyl 2-(1-methoxycarbonylpentoxy)benzoate as yellow oil. The colourless suspension was heated under reflux the suspension was filtered the residue was washed with acetone Concentration of the filtrate in vacuo resulted in 27.8 g (99% of theory) of methyl 2-(1-methoxycarbonylpentoxy)benzoate as yellow oil

Conditions: temp:105.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 2-bromocaproate (40 g) was added to anhydrous potassium fluoride (23 g) in acetamide (23 g) kept at 105° C. The mixture was vigorously stirred at 105° C. for 6 hours. The crude product obtained after the conventional work-up was distilled. Yield; 20 g (71 %), b.p.; 66° C./20 mmHg kept at 105° C

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

Procedure: To a solution of 2-bromo-hexanoic acid methyl ester (0.500 g, 2.404 mmol) and 4-fluoro-3-methylphenol (0.303 g, 2.404 mmol) in 15 mL of DMF, was added K2CO3 (1.661 g, 12.020 mmol). After stirring at room temperature under N2 for 88 h, the reaction mixture was diluted with 60 mL of water and extracted with dichloromethane (60 mL×3). The organic extracts were combined and dried over anhydrous Na2SO4. After removing the solvent under reduced pressure, the product was isolated by Flash chromatography (silica gel) eluting with 0-20% ethyl acetate/hexanes to give the title compound as yellow oil (0.467 g, 76% yield). LC-MS: tR=10.5 min; m/z 255 (M+H)+. extracted with dichloromethane (60 mL×3) dried over anhydrous Na2SO4 After removing the solvent under reduced pressure the product was isolated by Flash chromatography (silica gel) eluting with 0-20% ethyl acetate/hexanes