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CAS No. : | 2969-81-5 | MDL No. : | MFCD00000259 |
Formula : | C6H11BrO2 | Boiling Point : | 198.3°C at 760 mmHg |
Linear Structure Formula : | - | InChI Key : | N/A |
M.W : | 195.05 g/mol | Pubchem ID : | 76300 |
Synonyms : |
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Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P210-P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P370+P378-P403+P233-P403+P235-P405-P501 | UN#: | 1760 |
Hazard Statements: | H227-H315-H318-H335 | Packing Group: | Ⅲ |
GHS Pictogram: |
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Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.5% | With hydrogenchloride In 1,4-dioxane; ethanol; dichloromethane | Part A Preparation of ethyl 4-bromobutyrate To a solution of 4-bromobutyric acid (3 g, 18 mmol) in ethanol (30 mL) was added 5 mL of 4N HCl in dioxane. The reaction mixture was stirred for 16 hours at room temperature, and then the volatile components were removed under vacuum. The concentrated residue was brought up in 150 mL of methylene chloride. The organic solution was washed with saturated aqueous NaHCO3 (1 x 150 mL), brine (1*150 mL), dried over MgSO4, filtered, and the filtrate was concentrated at reduced pressure. The concentrated residue was dried in vacuo to give 3 g (85.5percent) of the known product as a yellow oil. 1 H NMR (300 MHz/CDCl3): δ 1.22 (t, 3H, J=7.15 Hz), 2.13 (overlapping t, 2H, J=6.80 Hz), 2.45 (t, 2H, J=7.15 Hz), 3.43 (t, 2H, J=6.44 Hz), 4.10 (q, 2H, J=7.25 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With potassium iodide In acetone for 12 h; Reflux | In a 100 ml round bottom flask, ethyl4-bromobutyrate (6.0 ml, 40.2 mmol: 1H NMR (300 MHz, CDCl3) δ 4.14(q, J = 7.2 Hz, 2H), 3.47 (t, J = 6.5 Hz, 2H), 2.49 (t, J = 7.2 Hz, 2H), 2.17(m, 2H), 1.26 (t, J = 7.1 Hz, 3H).) was dissolved in 40 ml acetone. Potassium iodide (13.35 g, 80.4 mmol,2.0 equiv.) was added, a reflux condenser was attached, and the reaction was heated at reflux for 12h. Thesolution was cooled, filtered through a course fritted funnel, and concentrated in vacuo. The resultingyellow oil with fine particulates was taken up in ca 50 ml of 1:1 Hex:Et2O and filtered through neutralaluminum to remove color. After flushing with an additional 100 ml 1:1 Hex:Et2O, the solution wasconcentrated to yield 8.44 g (87percent) of ethyl 4-iodobutyrate 12. 1H NMR (300 MHz, CDCl3) δ 4.14 (q, J =7.2 Hz, 2H), 3.24 (t, J = 6.8 Hz, 2H), 2.44 (t, J = 7.1 Hz, 2H), 2.13 (m, 2H), 1.26 (t, J = 7.2 Hz, 3H). A 50ml Schlenk flask was flame dried under vacuum, cooled to 23 °C, and charged with ethyl 4-iodobutyrate(8.4 g, 34.7 mmol) and copper(I) iodide (10 mg, 0.05 mmol). After sealing with a greased ground glassstopper, the flask was evacuated and refilled with Ar. The stopper was replaced with a rubber septum andneat diethyl zinc (14 ml, 137 mmol, 4 equiv) was added via syringe. The reaction was heated at 40 °C for12 h. The excess diethyl zinc and ethyl iodide were removed under vacuum for 2 h into a trap withmethanol cooled to -78 °C with dry ice and acetone. (CAUTION: A trap cooled with liquid nitrogeneasily clogs so dry ice/acetone cooling is preferred. Methanol quenches the excess diethyl zinc, but careshould be taken when cleaning the trap as some diethyl zinc may remain.) After backfilling with Ar, THF(5 ml) was added to the reaction vessel and heated at 40 °C for 1 h under Ar. The reaction vessel wasevacuated for 1 h. This step was repeated another two times. After cooling to 23 °C, the generated bis(4-ethoxy-4-oxobutyl)zinc was diluted with 15 ml of THF and this solution was used directly in thedesymmetrization reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With potassium carbonate In acetonitrile for 8 h; Reflux | To a solution of 4-chlorophenol (2.0 g, 15.556 mmol, 1 equiv) in acetonitrile (60 mL) was added anhydrous potassium carbonate (4.3 g, 31 .1 13 mmol, 2 equiv) and ethyl 4-bromobutanoate (3.56 mL, 24.891 mmol, 1 .6 equiv). The reaction mixture was heated to reflux and stirred for 8 h. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mixture was allowed to cool to 27 °C, filtered the solid and washed with ethyl acetate (100 mL). The filtrate was concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography using 10percent ethyl acetate in hexane as eluent to obtain the title compound ethyl 4-(4-chlorophenoxy)butanoate (3.5 g, 92 percent yield) as colourless liquid. LCMS (ES) m/z = 242.9 [M+H]+. NMR (400 MHz, CDCI3): δ ppm 1 .25 (t, J = 6.8 Hz, 3 H), 2.06 - 2.06 (m, 2 H), 2.49 (t, J = 6.8 Hz, 2 H), 3.97 (t, J = 6.0 Hz, 2 H), 4.1 1 - 4.17 (m, 2 H), 6.80 (d, J = 8.4 Hz, 2 H), 7.21 (d, J = 8.8 Hz, 2 H). |
89% | With potassium carbonate In N,N-dimethyl-formamide at 140℃; for 4 h; | To a solution of 4-chlorophenol (10 g, 77.784 mmol, 1 equiv) in N,N- dimethylformamide (100 mL) was added anhydrous potassium carbonate (21 .5 g, 1 16.6 mmol, 2 equiv) and ethyl 4-bromobutanoate (16.7 mL, 1 16.677 mmol, 1 .5 equiv). The reaction mixture was heated to 140 °C and stirred for 4 h. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mixture was allowed to cool to 27 °C, filtered the solid and washed with ethyl acetate (700 mL). The filtrate was washed with water (2 x 200 mL), brine solution (100 mL), dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography using 10 percent ethyl acetate in hexane as eluent to obtain ethyl 4-(4-chlorophenoxy)butanoate (17.0 g, 89 percent yield) as white solid. LCMS (ES) m/z = 243.1 [M+H]+. NMR (400 MHz, CDCI3): δ ppm 1 .25 (t, J = 7.2 Hz, 3 H), 2.06 - 2.12 (m, 2 H), 2.49 (t, J = 7.6 Hz, 2 H), 3.97 (t, J = 6.0 Hz, 2 H), 4.1 1 - 4.17 (m, 2 H), 6.80 (d, J = 8.8 Hz, 2 H), 7.21 (d, J = 8.8 Hz, 2 H). |
83% | With potassium carbonate In acetoneReflux | General procedure: General synthetic procedure for phenoxy acetic/butyric acid ethyl ester derivatives (3a-l) A mixture of substituted phenols 1a-f (0.05 mol) and 2a-b (0.075 mol) in dry acetone (40 ml) with anhydrous potassium carbonate (0.075 mol) were refluxed for 8-10 h. The reaction mixture was cooled and solvent removed by distillation. The residual mass was triturated with cold water to remove potassium carbonate, and extracted with ether (3 * 30 ml). The ether layer was washed with 10percent sodium hydroxide solution (3 * 30 ml) followed by water (3 * 30 ml) and then dried over anhydrous sodium sulfate and evaporated to afford compounds 3a-l. 4-(4-Chloro-phenoxy)-butyric acid ethyl ester (3b) Yield 83percent; FT-IR (cm-1): 1738 (C=O), 1281 (C-O-C); 1H NMR (CDCl3): δ 1.35 (t, 3H, CH3 of ester), 2.26 (m, 2H, CH2), 2.75 (t, 2H, COCH2), 4.07 (t, 2H, OCH2), 4.31 (q, 2H, CH2 of ester), 6.88 (d, J = 8.80 Hz, 2H, Ar-H), 7.27 (d, J = 8.85 Hz, 2H, Ar-H); LC-MS m/z 243 (M + 1). Anal. Calcd. for C12H15ClO3: C, 59.39; H, 6.23. Found: C, 59.50; H, 6.16percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With potassium carbonate In acetoneReflux | General procedure: General synthetic procedure for phenoxy acetic/butyric acid ethyl ester derivatives (3a-l) A mixture of substituted phenols 1a-f (0.05 mol) and 2a-b (0.075 mol) in dry acetone (40 ml) with anhydrous potassium carbonate (0.075 mol) were refluxed for 8-10 h. The reaction mixture was cooled and solvent removed by distillation. The residual mass was triturated with cold water to remove potassium carbonate, and extracted with ether (3 * 30 ml). The ether layer was washed with 10percent sodium hydroxide solution (3 * 30 ml) followed by water (3 * 30 ml) and then dried over anhydrous sodium sulfate and evaporated to afford compounds 3a-l. 4-(4-Bromo-phenoxy)-butyric acid ethyl ester (3d) Yield 81percent; FT-IR (cm-1): 1733 (C=O), 1287 (C-O-C); 1H NMR (CDCl3): δ 1.34 (t, 3H, CH3 of ester), 2.26 (m, 2H, CH2), 2.72 (t, 2H, COCH2), 4.05 (t, 2H, OCH2), 4.31 (q, 2H, CH2 of ester), 6.83 (d, J = 8.80 Hz, 2H, Ar-H), 7.35 (d, J = 8.85 Hz, 2H, Ar-H); LC-MS m/z 288 (M + 1). Anal. Calcd. for C12H15BrO3: C, 50.19; H, 5.27. Found: C, 50.29; H, 5.18percent. |