1,10-dibromodecane

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:

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: Synthesized as described above for compound 1. Quantities: K2CO3 (4.75 g, 34 mmol), p-hydroxybenzaldehyde (3.57 g, 29 mmol), 1,10-dibromodecane (8.6 mL, 38 mmol). Yield 10.0 g (quant.). 1H NMR: δH (CDCl3; 300 MHz): 1.22-1.52 (12 H, m, CH2), 1.80 (4 H, m, O—CH2—CH2/Br—CH2—CH2), 3.36 (2 H, t, 3J=6.9 Hz, Br—CH2), 4.00 (2 H, t, 3J=6.5 Hz, O—CH2), 6.95 (2 H, d, 3J=8.7 Hz, Ar—H), 7.79 (2 H, d, 3J =8.8 Hz, Ar—H), 9.84 (1 H, s, COH). 13C NMR: δC (CDCl3; 75 MHz): 25.9, 28.1, 28.7, 29.0, 29.3, 29.4, 29.5, 32.8, 34.0, 68.4, 114.7, 129.7, 131.9, 164.2, 190.7. Synthesized

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

Procedure: Sodium hydride (1.55 g, 61 mmol) was suspended in DMF (150 mL) under an atmosphere of nitrogen. Ethyl-4-hydroxybenzoate (11) (5.06 g, 30 mmol) was added as a solution in DMF (30 mL) via syringe which was then washed with DMF (2×5 mL). The reaction mixture was then stirred at room temperature under an atmosphere of nitrogen for 2 hours. After this time, 1,10-dibromodecane (30.84 g, 103 mmol) was added as a solution in DMF (50 mL) via syringe which was then washed with DMF (2×5 mL). The reaction mixture was then stirred at room temperature under nitrogen for 19 hours. The reaction was quenched with water (200 mL) and the organic fragments extracted with diethyl ether (4×150 mL), dried over MgSO4, and excess solvent removed in vacuo to form a colorless oil. This was purified by flash column chromatography using CH2Cl2/hexane (1:1) to CH2Cl2/hexane (3:1) as eluting solvents to form a white crystalline solid. This was recrystallized from ethanol to form 4-(10-bromo-decyloxy)-benzoic acid ethyl ester (7.38 g, 19.1 mmol, 63%). Rf 0.65 (CH2Cl2), mp 41-42° C. FTIR, νmax/cm−1 1 3023, 2927, 2855, 1708, 1604, 1509, 1468, 1390, 1367, 1312, 1252, 1155, 1018, 851, 772. 1H NMR (CDCl3, 250 MHz), δ/ppm 7.96 and 6.87 (both 2 H, m, Ar—H); 4.32 (2 H, q, 3J=7.1 Hz, −CH2CH3); 3.97 (2 H, t, 3J=6.5 Hz, —OCH2—); 3.38 (2 H, t, 3J=6.9 Hz, —CH2Br); 1.80 (4 H, m, —OCH2CH2— and —CH2CH2Br); 1.42-1.27 (15 H, m, alkyl C—H). 13C{1H} NMR (CDCl3, 63 MHz), δ/ppm 166.2 (C=O); 152.6 and 122.4 (quat. Ar C); 131.3 and 113.8 (Ar C—H); 67.9 and 60.4 (—OCH2—); 33.9, 32.6, 29.2, 29.1, 29.0, 28.9, 28.5, 28.0, 25.8 (CH2); 14.2 (—CH3) λmax/nm (ε/dm3mol−1cm−1) 257 (24641). HRMS (FAB), M+/z C19H30BrO3 (MH+) requires 385.1378, found 385.1374. was then washed with DMF (2×5 mL) was then washed with DMF (2×5 mL) The reaction mixture was then stirred at room temperature under nitrogen for 19 hours The reaction was quenched with water (200 mL) the organic fragments extracted with diethyl ether (4×150 mL) dried over MgSO4, and excess solvent removed in vacuo to form a colorless oil This was purified by flash column chromatography as eluting solvents to form a white crystalline solid This was recrystallized from ethanol

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

Procedure: To a 250 mL flask in ice-water bath was added 1,10-dibromodecane (46.0 g, 153 mmol) and anhydrous THF (100 ml) under nitrogen. Phenyl lithium (1.8 M in dibutyl ether, 28.5 mL, 51 mmol) was added dropwise. After addition was completed, the reaction mixture was stirred for 1 hour and warmed to room temperature. After 48 hours, it was quenched with H2O (200 mL), extracted with CH2Cl2 (200 mL×2) and dried. After concentration, the residue was distilled to give a colorless oil (9.35 g, yield 61.7%) at 130° C./0.07 mmHg. 1H NMR (CDCl3, 500 MHz) δ=7.27-7.32 (m, 2H), 7.20 (d, J=6.5 Hz, 3H), 3.43 (t, J=7.0 Hz, 2H), 2.62 (t, J=8.0 Hz, 2H), 1.84-1.96 (m, 2H), 1.60-1.68 (m, 2H), 1.41-1.52 (m, 2H), 1.24-1.41 (m, 10H). After addition After 48 hours it was quenched with H2O (200 mL) extracted with CH2Cl2 (200 mL×2) dried After concentration the residue was distilled

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

Procedure: To a 1 L Morton flask was added diallylmethylamine (86.1 g), 1,10-dibromodecane (112 g), and methanol (100 mL). The mixture was heated to 65° C. for 24 h, and then allowed to cool to room temperature. The solvent was removed by rotary vacuum evaporation. Diethylether (400 mL) was added and the mixture was stirred for 1 hr. The mixture was allowed to settle and the top layer was decanted and discarded. The remaining oil was dried by rotary vacuum evaporation to yield 215 g of product. to cool to room temperature The solvent was removed by rotary vacuum evaporation Diethylether (400 mL) was added the top layer was decanted The remaining oil was dried by rotary vacuum evaporation

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

Procedure: 25.4 g (0.1 mol) diethyl-2,5-dihydroxyterephthalate, 450 g (1.5 mol) 1,10-dibromodecane, 138 g (1.0 mol) K2CO3 and 200 mg NaI in 200 ml acetone are heated under reflux for 28 hours until the originally yellow suspension has decolorized. After distilling off the solvent, the reaction mixture is extracted twice with diethyl ether (2×250 ml), and insoluble salts are filtered off. The filtrate is washed twice with 200 ml water and dried over Na2SO4. The solvent is then distilled off. The colourless, solid residue is washed twice with petroleum ether and then recrystallized from petroleum ether. under reflux for 28 hours until the originally yellow suspension After distilling off the solvent the reaction mixture is extracted twice with diethyl ether (2×250 ml), and insoluble salts are filtered off The filtrate is washed twice with 200 ml water dried over Na2SO4 The solvent is then distilled off The colourless, solid residue is washed twice with petroleum ether recrystallized from petroleum ether