11-bromoundecanoyl chloride

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 11-bromoundecanoic acid (10.00 g, 37.7 mmol) dissolved in CH2Cl2 (30 mL) was slowly added to a solution of SOCl2 (7.0 mL, 94.0 mmol) in CH2Cl2 (25 mL). The mixture was refluxed for 5 h, then concentrated in vacuo to give 11-bromoundecanoyl chloride, which was used without further purification: 1H NMR (CDCl3) δ 1.26 (bs, (CH2)5, 10H), 1.34 (m, CH2CH2CH2Br, 2H), 1.67 (m, CH2CH2COCl, 2H), 1.81 (m, CH2CH2Br, 2H), 2.85 (t, CH2COCl, J=7.2 Hz, 2H), 3.36 (t, CH2Br, J=6.8 Hz, 2H); 13C NMR (CDCl3) δ 24.89 (CH2CH2COCl), 27.95 (CH2CH2CH2Br), 28.21, 28.52, 28.84, 29.02, and 29.12 ((CH2)5), 32.64 (CH2CH2Br), 33.80 (CH2Br), 46.92 (CH2COCl), 173.47 (COCl). The mixture was refluxed for 5 h concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 11-bromoundecanoic acid (10.00 g, 37.7 mmol) dissolved in CH2Cl2 (30 mL) was slowly added to a solution of SOCl2 (7.0 mL, 94.0 mmol) in CH2Cl2 (25 mL). The mixture was refluxed for 5 h, then concentrated in vacuo to give 11-bromoundecanoyl chloride, which was used without further purification: 1H NMR (CDCl3) δ 1.26 (bs, (CH2)5, 10 H), 1.34 (m, CH2CH2CH2Br, 2 H), 1.67 (m, CH2CH2COCl, 2 H), 1.81 (m, CH2CH2Br, 2 H), 2.85 (t, CH2COCl, J=7.2 Hz, 2 H), 3.36 (t, CH2Br, J=6.8 Hz, 2 H); 13C NMR (CDCl3) δ 24.89 (CH2CH2COCl), 27.95 (CH2CH2CH2Br), 28.21, 28.52, 28.84, 29.02, and 29.12 ((CH2)5), 32.64 (CH2CH2Br), 33.80 (CH2Br), 46.92 (CH2COCl), 173.47 (COCl). The mixture was refluxed for 5 h concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 11-bromoundecanoic acid (10.00 g, 37.7 mmol) dissolved in CH2Cl2 (30 mL) was slowly added to a solution of SOCl2 (7.0 mL, 94.0 mmol) in CH2Cl2 (25 mL). The mixture was refluxed for 5 h, then concentrated in vacuo to give 11-bromoundecanoyl chloride, which was used without further purification: 1H NMR (CDCl3) δ1.26 (bs, (CH2)5, 10H), 1.34 (m, CH2CH2CH2Br, 2H), 1.67 (m, CH2CH2COCl, 2H), 1.81 (m, CH2CH2Br, 2H), 2.85 (t, CH2COCl, J=7.2 Hz, 2H), 3.36 (t, CH2Br, J=6.8 Hz, 2H); 13C NMR (CDCl3) δ24.89 (CH2CH2COCl), 27.95 (CH2CH2CH2Br), 28.21, 28.52, 28.84, 29.02, and 29.12 ((CH2)5) 32.64 (CH2CH2Br), 33.80 (CH2Br), 46.92 (CH2COCl), 173.47 (COCl). The mixture was refluxed for 5 h concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 11-Bromoundecanoic acid (400 g) was added to thionyl chloride (600 ml) and the solution heated at 80° for 0.5 hour. The thionyl chloride was distilled off and the dark oily residue distilled in vacuo to give 11-bromoundecanoyl chloride, b.p. 144°, 0.7 mm Hg, (346.8 g, 81%). the solution heated at 80° for 0.5 hour The thionyl chloride was distilled off the dark oily residue distilled in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 11-bromoundecanoic acid (10.00 g, 37.7 mmol) dissolved in CH2Cl2 (30 mL) was slowly added to a solution of SOCl2 (7.0 mL, 94.0 mmol) in CH2Cl2 (25 mL). The mixture was refluxed for 5 h, then concentrated in vacuo to give 11-bromoundecanoyl chloride, which was used without further purification: The mixture was refluxed for 5 h concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 11-bromoundecanoic acid (10.00 g, 37.7 mmol) dissolved in CH2Cl2 (30 mL) was slowly added to a solution of SOCl2 (7.0 mL, 94.0 mmol) in CH2Cl2 (25 mL). The mixture was refluxed for 5 h, then concentrated in vacuo to give 11-bromoundecanoyl chloride, which was used without further purification: The mixture was refluxed for 5 h concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 20 g. of 11-bromoundecanoyl chloride in 100 ml. of methylene chloride is slowly added with stirring to a solution of 20 g. of ethyl 4-aminobenzoate in 100 ml. of methylene chloride. The mixture is filtered and the filtrate is washed with dilute hydrochloric acid and water, dried, and evaporated. Crystallization from acetonitrile affords ethyl 4-(11-bromoundecanamido)benzoate as a white solid. The mixture is filtered the filtrate is washed with dilute hydrochloric acid and water dried evaporated Crystallization from acetonitrile

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 28 g. of 11-bromoundecanoyl chloride in 100 ml. of methylene chloride is slowly added with stirring to a solution of 20 g. of ethyl 4-aminobenzoate in 100 ml. of methylene chloride. The mixture is filtered and the filtrate is washed with dilute hydrochloric acid and water, dried, and evaporated. Crystallization from acetonitrile affords ethyl 4-(11-bromoundecanamido)benzoate as a white solid. The mixture is filtered the filtrate is washed with dilute hydrochloric acid and water dried evaporated Crystallization from acetonitrile

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 28 g. of 11-bromoundecanoyl chloride in 100 ml. of methylene chloride is slowly added with stirring to a solution of 20 g. of ethyl 4-aminobenzoate in 100 ml. of methylene chloride. The mixture is filtered and the filtrate is washed with dilute hydrochloric acid and water, dried, and evaporated. Crystallization from acetonitrile affords ethyl 4-(11-bromoundecanamido)benzoate as a white solid. The mixture is filtered the filtrate is washed with dilute hydrochloric acid and water dried evaporated Crystallization from acetonitrile

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 55 g (0.20 moles) of recrystallised 11-bromo undecanoic acid were refluxed with 48 g (0.4 moles) of thionyl chloride for 3 hours. Excess thionyl chloride was then removed by vacuum distillation at 10-14 mm Hg pressure. The crude acid chloride remaining was distilled under higher vacuum (0.1 mm Hg) to give 50 g (0.18 moles) of pure 11-bromo undecanoyl chloride. Excess thionyl chloride was then removed by vacuum distillation at 10-14 mm Hg pressure The crude acid chloride remaining was distilled under higher vacuum (0.1 mm Hg)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 11-bromoundecanoic acid (10.00 g, 37.7 mmol) dissolved in CH2Cl2 (30 mL) was slowly added to a solution of SOCl2 (7.0 mL, 94.0 mmol) in CH2Cl2 (25 mL). The mixture was refluxed for 5 h, then concentrated in vacuo to give 11-bromoundecanoyl chloride, which was used without further purification: 1H NMR (CDCl3) δ 1.26 (bs, (CH2)5, 10H), 1.34 (m, CH2CH2CH2Br, 2H), 1.67 (m, CH2CH2COCl, 2H), 1.81 (m, CH2CH2Br, 2H), 2.85 (t, CH2COCl, J=7.2 Hz, 2H), 3.36 (t, CH2Br, J=6.8 Hz, 2H); 13C NMR (CDCl3) δ 24.89 (CH2CH2COCl), 27.95 (CH2CH2CH2Br), 28.21, 28.52, 28.84, 29.02, and 29.12 ((CH2)5), 32.64 (CH2CH2Br), 33.80 (CH2Br), 46.92 (CH2COCl), 173.47 (COCl). The mixture was refluxed for 5 h concentrated in vacuo