1-bromotridecane

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

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.3 g. Sodium are dissolved by warming in 44 ml. butane-1,4-diol, 38 ml. 1-bromotridecane are added thereto and the reaction mixture is stirred for 5 hours at a bath temperature of 150° C. After cooling, extraction is carried out with a mixture of diethyl ether-ligroin (1:2 v/v), the extract is evaporated and the residue is purified on a silica gel column by elution with ligroin which is subsequently replaced by diethyl ether-ligroin (1:1 v/v). The desired fractions are collected and evaporated. 19.4 g. (71% of theory) of thin layer chromatographically uniform 4-tridecyloxybutanol are thus obtained; m.p. 26°-29° C. by warming in 44 ml After cooling extraction is carried out with a mixture of diethyl ether-ligroin (1:2 v/v) the extract is evaporated the residue is purified on a silica gel column by elution with ligroin which The desired fractions are collected evaporated

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

Procedure: To a stirred, room temperature suspension of sodium nitrite (227 g, 3.29 mol) in dimethylformamide (3.8 L) was added 1-bromotridecane (514.51 g, 1.95435 mol), and the mixture was stirred for 6 hours. The mixture was poured into cold water (8 L) and extracted with petroleum ether (2×2 L). The organic layer was washed with water (2 L), saturated sodium chloride, dried (MgSO4), and rotoevaporated to a yellow oil. The oil was distilled in vacuo to give another oil; yield 171.9 g, bp 101°-120° C. (0.2 mm Hg). The oil was chromatographed on silica gel (3.0 kg, 230-400 mesh) using ether/ethyl acetate (100:1, 4×2 L; 80:1, 4×2 L; 50:1, 7×2 L) to give a clear colorless oil; yield 109.8 g (24.5%). extracted with petroleum ether (2×2 L) The organic layer was washed with water (2 L), saturated sodium chloride dried (MgSO4) The oil was distilled in vacuo to give another oil The oil was chromatographed on silica gel (3.0 kg, 230-400 mesh) to give a clear colorless oil

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

Procedure: To a stirred, room temperature suspension of sodium nitrite (227 g, 3.29 mol) in dimethylformamide (3.8 L) was added 1-bromotridecane (514.51 g, 1.95435 mol), and the mixture was stirred for 6 hours. The mixture was poured into cold water (8 L) and extracted with petroleum ether (2×2 L). The organic layer was washed with water (2 L), saturated sodium chloride, dried (MgSO4), and rotoevaporated to a yellow oil. The oil was distilled in vacuo to give another oil; yield 171.9 g, bp 101°-120° C. (0.2 mm Hg). The oil was chromatographed on silica gel (3.0 kg, 230-400 mesh) using ether/ethyl acetate (100:1, 4×2 L; 80:1, 4×2 L; 50:1, 7×2 L) to give a clear colorless oil; yield 109.8 g (24.5%). extracted with petroleum ether (2×2 L) The organic layer was washed with water (2 L), saturated sodium chloride dried (MgSO4) The oil was distilled in vacuo to give another oil The oil was chromatographed on silica gel (3.0 kg, 230-400 mesh) to give a clear colorless oil

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

Procedure: This was prepared using a similar method to that described for compound 3. Quantities: compound 1 (4.02 g, 21.1 mmol), 1-bromotridecane (6.11 g, 23.2 mmol), potassium carbonate (5.22 g, 37.8 mmol) and butanone (115 ml). This was prepared

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

Procedure: 5,10,15,20-tetrakis-(4-Hydroxy-phenyl)-porphyrin (400 mg, 0.59 mmol) is dissolved and K2CO3 (1.0 g, 7.1 mmol) is suspended in DMF (75 mL). To the vigorously stirred reaction mixture a solution of 1-bromotridecane (0.1 mL, 0.45 mmol) in DMF (10 mL) is added dropwise at 50° C. during 30 mins and the mixture is then heated for 1.5 h. The reaction mixture is cooled to room temperature and poured into water (150 mL). The porphyrins are extracted with ethyl acetate (100 mL) and the extract washed with brine (3×50 mL) and dried (Na2SO4). After evaporation of solvent, the residue is dissolved in toluene:ethanol (1:1, by vol., ca. 10 mL) and purified by chromatography using a column (200 g) of silica gel (Merck 60) with toluene as the eluent. After the elution of the first three compounds, the eluent is changed to toluene:ethyl acetate (2:1, by vol.). The fifth compound eluted is collected and dried under high vacuum to yield product as a violet solid. is added dropwise at 50° C. during 30 mins the mixture is then heated for 1.5 h The porphyrins are extracted with ethyl acetate (100 mL) the extract washed with brine (3×50 mL) dried (Na2SO4) After evaporation of solvent the residue is dissolved in toluene:ethanol (1:1, by vol., ca. 10 mL) purified by chromatography After the elution of the first three compounds The fifth compound eluted is collected dried under high vacuum to yield product as a violet solid

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

Procedure: N-Tridecylcarbazole was prepared from carbazole (62.43 g, 0.37 mol), 1-bromotridecane (100 g, 0.38 mol, commercially available from Aldrich, Milwaukee, Wis.), benzyltriethyl ammonium chloride (4.24 g. 0.018 mol), toluene (400 ml), and 50% aqueous NaOH (200 g) according to the procedure described for N-heptylcarbazole. The product was obtained as 120 g of brown liquid (96% yield).

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

Procedure: N-Tridecylcarbazole was prepared from carbazole (62.43 g, 0.37 mol), 1-bromotridecane (100 g, 0.38 mol, commercially available from Aldrich, Milwaukee, Wis.), benzyltriethyl ammonium chloride (4.24 g. 0.018 mol), toluene (400 ml), and 50% aqueous NaOH (200 g) according to the procedure described for N-heptylcarbazole. The product was obtained as 120 g of brown liquid (96% yield).

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

Procedure: A solution of 1-bromotridecane (100 g, 0.4 mol) and triphenyl phosphine (100 g, 0.4 mol) in 500 ml of xylenes was refluxed overnight. The reaction mixture was then cooled to room temperature and poured into diethyl ether. The resulting oil was washed three times with ether, dissolved in methylene chloride and then concentrated in vacuo. The oil was left standing in diethyl ether at 0° C. overnight and then concentrated in vacuo to give a white solid. The resulting oil was washed three times with ether dissolved in methylene chloride concentrated in vacuo The oil was left concentrated in vacuo to give a white solid

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

Procedure: A solution of 1-bromotridecane (100 g, 0.4 mol) and triphenyl phosphine (100 g, 0.4 mol) in 500 ml of xylenes was refluxed overnight. The reaction mixture was then cooled to room temperature and poured into diethyl ether. The resulting oil was washed three times with ether, dissolved in methylene chloride and then concentrated in vacuo. The oil was left standing in diethyl ether at 0° C. overnight and then concentrated in vacuo to give a white solid. The resulting oil was washed three times with ether dissolved in methylene chloride concentrated in vacuo The oil was left concentrated in vacuo to give a white solid

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

Procedure: According to the method of Example 26, from aldehyde 4 (332 mg, 1.31 mmol) and 1-bromotridecane (863 mg, 3.28 mmol), alcohol 33 was obtained as a colorless oil (172 mg, 30% yield).

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

Procedure: According to the method of Example 26, from aldehyde 4 (332 mg, 1.31 mmol) and 1-bromotridecane (863 mg, 3.28 mmol), alcohol 33 was obtained as a colorless oil (172 mg, 30% yield).