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CAS No. : | 253429-18-4 | MDL No. : | MFCD14584680 |
Formula : | C12H16BrFO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 307.16 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With polyphosphoric acid In toluene for 5 h; Reflux | A solution of 2-Bromo-5-fluorophenol (228.00 g, 1.19 mol), Potassium carbonate (247.47 g, 1.79 mol) in N,N-Dimethylformamide (3.00 L) was treated with 2-Bromo-1,1-diethoxyethane (197.54 mL, 1.31 mol) and heated at 135 °C for 7 h. The reaction mixture was concentrated in vacuo and extracted with EtOAc (3 * 2 L). The combined organic layers were washed with aq NaOH (2 M, 4 L). The organic layer was dried (MgSO4), filtered, concentrated in vacuo to yield 1-Bromo-2-(2,2-diethoxyethoxy)-4-fluorobenzene (362.00 g; Yield = 98percent) that was used as it is in the next step. 1H NMR (400 MHz, D6-DMSO) δ 7.58 (d, 1H, J = 6.8 & 8.8 Hz), 7.11 (dd, 1H, J = 2.8 & 10.8 Hz), 6.76 (dt, 1H, J = 2.2 & 8.1 Hz), 4.81 (t, 1H, J = 5.1 Hz), 4.03 (d, 2H, J = 5.1 Hz), 3.73-3.56 (m, 4H), 1.13 (t, 6H, J = 6.6 Hz). A solution of 1-Bromo-2-(2,2-diethoxyethoxy)-4-fluorobenzene (352.00 g, 1.15 mol) in toluene (2500 mL, 2.3 mol) was treated with polyphosphoric acid (370.00 g, 3.4 mol) and heated at reflux for 5 h. The reaction mixture was concentrated in vacuo diluted with water (3 L) and the extracted with EtOAc (4 L). The organic layer was washed with aq NaOH (2 L), filtered, concentrated in vacuo and purified by distillation at reduced pressure to yield (4) 7-bromo-4-fluorobenzofuran (125.00 g; Yield = 51percent. bp 80 °C (1 mm/Hg) as a colorless liquid which solidified at rt. 1H NMR (400 MHz, CDCl3) δ 7.67 (d, 1H, J = 2.2 Hz), 7.39 (dd, 1H J = 5.1 & 3.7 Hz), 6.94 (d, 1H, J = 2.2 Hz), 6.86 (t, 1H, J = 8.8 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With Amberlyst-15; In chlorobenzene;Heating / reflux; | A mixture of 109.4 gm Amberlyst-15 in 707 mL chlorobenzene was heated at reflux to remove water by azeotropic distillation. Distillate was removed until the volume remaining in the pot was about 500 mL. To this mixture was then added dropwise over 2 hours a solution of 109.4 gm (356 mMol) <strong>[253429-18-4]2-(2-bromo-4-fluorophenoxy)acetaldehyde diethyl acetal</strong> in 4060 mL chlorobenzene. The mixture was stirred at reflux with constant water removal. When no more water was observed in the azeotrope distillate, the reaction mixture was cooled to room temperature. The filter cake was washed with 400 mL dichloromethane and the combined filtrates were concentrated under reduced pressure to provide 102 gm of a colorless oil. This oil was diluted with 500 mL hexane and subjected to silica gel chromatography, eluting with hexane. Fractions containing the desired product were combined and concentrated under reduced pressure to provide 39.6 gm (52%) of the title compound.1H-NMR(CDCl3): delta 7.75 (d, J=2.1 Hz, 1H), 7.27 (dd, JH,H=2.5 Hz, JH,F=8.8 Hz, 1H), 7.25 (dd, JH,H=2.5 Hz, JH,F=8.3 Hz, 1H), 6.85 (d, J=2.2 Hz, 1H). |
52% | With amberlyst-15; In chlorobenzene;Heating / reflux; water removal by azeotropic distillation; | A mixture of 109.4 gm Amberlyst-15 in 707 mL chlorobenzene was heated at reflux to remove water by azeotropic distillation. Distillate was removed until the volume remaining in the pot was about 500 mL. To this mixture was then added dropwise over 2 hours a solution of 109.4 gm (356 mMol) <strong>[253429-18-4]2-(2-bromo-4-fluorophenoxy)acetaldehyde diethyl acetal</strong> in 4060 mL chlorobenzene. The mixture was stirred at reflux with constant water removal. When no more water was observed in the azeotrope distillate, the reaction mixture was cooled to room temperature. The filter cake was washed with 400 mL dichloromethane and the combined filtrates were concentrated under reduced pressure to provide 102 gm of a colorless oil. This oil was diluted with 500 mL hexane and subjected to silica gel chromatography, eluting with hexane. Fractions containing the desired product were combined and concentrated under reduced pressure to provide 39.6 gm (52%) of the title compound.1H-NMR(CDCl3): delta 7.75 (d, J = 2.1 Hz, 1H), 7.27 (dd, JH,H = 2.5 Hz, JH,F = 8.8 Hz, 1H), 7.25 (dd, JH,H = 2.5 Hz, JH,F = 8.3 Hz, 1H), 6.85 (d, J = 2.2 Hz, 1H). |
Scheme I, step B. A 500 mL round bottom flask was charged with chlorobenzene (120 mL) and polyphosphoric acid (40.0 g), and the mixture was heated to reflux. To the refluxing mixture was added dropwise <strong>[253429-18-4]2-(2-bromo-4-fluorophenol) acetaldehyde diethyl acetal</strong> (48.3 g, 0.16 mol, prepared in Scheme I, step A above) dissolved in chlorobenzene (60 mL). After refluxing for 2 hours at room temperature, the reaction mixture was cooled to room temperature and poured into 1N sodium hydroxide. The reaction mixture was then stirred for 16 hours, extracted with diethyl ether, the organic extracts were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by flash chromatography (hexane, silica gel) to provide 5-fluoro-7-bromo-benzo(b)furan (9.3 g) as a clear oil. |
With AMBERLYST 15 ion exchange resin; In chlorobenzene;Reflux; | Step 2: A mixture of AMBERLYST 15 ion exchange resin (25 g) in chlorobenzene (150 mL)was heated at reflux to remove water by azeotropic distillation. Then to this mixture, a solutionof S19-1 (25 g, 0.08 mol) in chlorobenzene (1000 mL) was added dropwise over 2 hrs. The mixture was stirred at reflux with constant removal of water. Then the mixture was cooled to room temperature. The filtered cake was washed with dichloromethane (200 mL) and the combined filtrate was concentrated to obtain S19-2, which was purified by column chromatography (eluted with petroleum). | |
With AMBERLYST 15 ion exchange resin; In chlorobenzene; for 2h;Reflux; | Step 2: A mixture of AMBERLYST 15 ion exchange resin (25 g) in chlorobenzene (150 mL) was heated at reflux to remove water by azeotropic distillation. Then to this mixture, a solution of S19-1 (25 g, 0.08 mol) in chlorobenzene (1000 mL) was added dropwise over 2 hrs. The mixture was stirred at reflux with constant removal of water. Then the mixture was cooled to room temperature. The filtered cake was washed with dichloromethane (200 mL) and the combined filtrate was concentrated to obtain SI 9-2, which was purified by column chromatography (eluted with petroleum). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.7% | With potassium carbonate; In N,N-dimethyl-formamide; for 18h;Heating / reflux; | To a solution of 20 gm (105 mMol) <strong>[496-69-5]2-bromo-4-fluorophenol</strong> in 211 mL dimethylformamide were added 15.8 mL (105 mMol) bromoacetaldehyde diethyl acetal followed by 14.5 gm (105 mMol) anhydrous potassium carbonate. This mixture was then heated at reflux for about 18 hours under a nitrogen atmosphere. The reaction mixture was then concentrated under reduced pressure and the resulting residue partitioned between 200 mL of ethyl acetate and 200 mL 1N sodium hydroxide. The phases were separated and the ethyl acetate phase was washed with 200 mL of water, giving rise to an emulsion. An additional 100 mL ethyl acetate and 20 mL of water were added to the emulsion. The separated ethyl acetate phase and emulsion were removed and saved. The ethyl acetate phase was washed again with 200 mL of water. This new emulsion was combined with the original emulsion and aqueous phase. The mixture was partitioned between 700 mL ethyl acetate and 780 mL of water. The emulsion and aqueous layer (1600 mL) were removed. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure to provide 26.4 gm (82%) of the desired material as an amber oil. The reserved emulsion and aqueous phase was washed with 1 L of toluene. The phases were separated and organic phase was dried over magnesium sulfate and concentrated under reduced pressure to provide an additional 4.67 gm of the desired compound as an amber oil. Total recovery of desired product was 31.1 gm (96.7%). |
96.7% | With potassium carbonate; In DMF (N,N-dimethyl-formamide); for 18h;Heating / reflux; | To a solution of 20 gm (105 mMol) <strong>[496-69-5]2-bromo-4-fluorophenol</strong> in 211 mL dimethylformamide were added 15.8 mL (105 mMol) bromoacetaldehyde diethyl acetal followed by 14.5 gm (105 mMol) anhydrous potassium carbonate. This mixture was then heated at reflux for about 18 hours under a nitrogen atmosphere. The reaction mixture was then concentrated under reduced pressure and the resulting residue partitioned between 200 mL of ethyl acetate and 200 mL 1N sodium hydroxide. The phases were separated and the ethyl acetate phase was washed with 200 mL of water, giving rise to an emulsion. An additional 100 mL ethyl acetate and 20 mL of water were added to the emulsion. The separated ethyl acetate phase and emulsion were removed and saved. The ethyl acetate phase was washed again with 200 mL of water. This new emulsion was combined with the original emulsion and aqueous phase. The mixture was partitioned between 700 mL ethyl acetate and 780 mL of water. The emulsion and aqueous layer (1600 mL) were removed. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure to provide 26.4 gm (82%) of the desired material as an amber oil. The reserved emulsion and aqueous phase was washed with 1L of toluene. The phases were separated.and organic phase was dried over magnesium sulfate and concentrated under reduced pressure to provide an additional 4.67 gm of the desired compound as an amber oil. Total recovery of desired product was 31.1 gm (96.7%). |
Scheme I, step A: A 500 mL round bottom flask was charged with sodium hydride (8.69 g of a 60% dispersion, 0.217 mol) and anhydrous DMF (130 mL), and the suspension was cooled to 0 C. To the cooled stirring suspension was added <strong>[496-69-5]2-bromo-4-fluorophenol</strong> (39.5 g, 0.207 mmol) dissolved in anhydrous DMF (20 mL). The reaction was stirred for 30 minutes after addition and then bromoacetaldehyde diethyl acetal (42.8 g, 0.217 mol) was added. The reaction was then heated at reflux for 2.5 hours, cooled to room temperature, and stirred for 24 hours. The reaction mixture was then poured into water and extracted with ethyl acetate (2×200 mL). The organic extracts were combined, washed with water (5×100 mL), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by flash chromatography to provide 2-(<strong>[496-69-5]2-bromo-4-fluorophenol</strong>) acetaldehyde diethyl acetal (53.3 g). |
With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 3h; | Step 1: To a solution of <strong>[496-69-5]2-bromo-4-fluorophenol</strong> (S19-SM, 50 g, 0.26 mol) and 2-bromo-1,1- diethoxyethane (129 g, 0.65 mol) in DMF was added K2C03 (72 g, 0.52 mol) in portion. Themixture was stirred at 120 C for 3 hrs. After cooling, the mixture was poured into water, and extracted with ethyl acetate. The organic layer was washed with brine, separated, dried over anhydrous sodium sulfate, filtered and concentrated to obtain S19-1, which was purified by column chromatography (petroleum: ethyl acetate = 20:1). | |
With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 3h; | Step 1: To a solution of <strong>[496-69-5]2-bromo-4-fluorophenol</strong> (S19-SM, 50 g, 0.26 mol) and 2-bromo-l,l- diethoxyethane (129 g, 0.65 mol) in DMF was added K2CO3 (72 g, 0.52 mol) in portion. The mixture was stirred at 120 C for 3 hrs. After cooling, the mixture was poured into water, and extracted with ethyl acetate. The organic layer was washed with brine, separated, dried over anhydrous sodium sulfate, filtered and concentrated to obtain SI 9-1, which was purified by column chromatography (petroleum : ethyl acetate = 20: 1). | |
26.4 gm (82%) | With sodium hydroxide; potassium carbonate; In N-methyl-acetamide; water; ethyl acetate; toluene; | 2-(2-bromo-4-fluorophenoxy)acetaldehyde diethyl acetal To a solution of 20 gm (105 mMol) <strong>[496-69-5]2-bromo-4-fluorophenol</strong> in 211 mL dimethylformamide were added 15.8 mL (105 mMol) bromoacetaldehyde diethyl acetal followed by 14.5 gm (105 mMol) anhydrous potassium carbonate. This mixture was then heated at reflux for about 18 hours under a nitrogen atmosphere. The reaction mixture was then concentrated under reduced pressure and the resulting residue partitioned between 200 mL of ethyl acetate and 200 mL 1N sodium hydroxide. The phases were separated and the ethyl acetate phase was washed with 200 mL of water, giving rise to an emulsion. An additional 100 mL ethyl acetate and 20 mL of water were added to the emulsion. The separated ethyl acetate phase and emulsion were removed and saved. The ethyl acetate phase was washed again with 200 mL of water. This new emulsion was combined with the original emulsion and aqueous phase. The mixture was partitioned between 700 mL ethyl acetate and 780 mL of water. The emulsion and aqueous layer (1600 mL) were removed. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure to provide 26.4 gm (82%) of the desired material as an amber oil. The reserved emulsion and aqueous phase was washed with 1L of toluene. The phases were separated and organic phase was dried over magnesium sulfate and concentrated under reduced pressure to provide an additional 4.67 gm of the desired compound as an amber oil. Total recovery of desired product was 31.1 gm (96.7%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.9% | A solution of 7-bromo-4-fluorobenzofuran (4) (124.12 g, 577.25 mmol) in ether (2.0 L) was cooled to -78 C and treated drop wise with a solution of 2.5 M of n-Butyllithium in Hexane (235.5 mL) and stirred at -78 C for 15 min. To this reaction mixture was added N,N-Dimethylformamide (89.393 mL, 1.15 mol) and stirred at -78 C for 30 min. The reaction mixture was quenched with methanol (23.383 mL, 577.25 mmol) and warmed to rt. It was diluted with ether (300 ml) and the organic layer was washed with water (300 mL). The seperated organic layer was dried (MgSO4) filtered, concentrated in vacuo to yield 4-Fluorobenzofuran-7-carbaldehyde (5) (89.00 g; Yield = 93.9%). Analysis of the product by 1H NMR indicated that the reaction mixture was pure. It was therefore taken to the next step as it is. 1H NMR 10.35 (s, 1H), 7.81 (dd, 1H, J = 5.2 & 8.0 Hz), 7.76 (d, 1H, J = 2.0 Hz), 7.07 (t, 1H, J = 8.8 Hz), 6.95 (d, 1H, J = 2.2 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With polyphosphoric acid; In toluene; for 5h;Reflux; | A solution of 2-Bromo-5-fluorophenol (228.00 g, 1.19 mol), Potassium carbonate (247.47 g, 1.79 mol) in N,N-Dimethylformamide (3.00 L) was treated with 2-Bromo-1,1-diethoxyethane (197.54 mL, 1.31 mol) and heated at 135 C for 7 h. The reaction mixture was concentrated in vacuo and extracted with EtOAc (3 * 2 L). The combined organic layers were washed with aq NaOH (2 M, 4 L). The organic layer was dried (MgSO4), filtered, concentrated in vacuo to yield 1-Bromo-2-(2,2-diethoxyethoxy)-4-fluorobenzene (362.00 g; Yield = 98%) that was used as it is in the next step. 1H NMR (400 MHz, D6-DMSO) delta 7.58 (d, 1H, J = 6.8 & 8.8 Hz), 7.11 (dd, 1H, J = 2.8 & 10.8 Hz), 6.76 (dt, 1H, J = 2.2 & 8.1 Hz), 4.81 (t, 1H, J = 5.1 Hz), 4.03 (d, 2H, J = 5.1 Hz), 3.73-3.56 (m, 4H), 1.13 (t, 6H, J = 6.6 Hz). A solution of 1-Bromo-2-(2,2-diethoxyethoxy)-4-fluorobenzene (352.00 g, 1.15 mol) in toluene (2500 mL, 2.3 mol) was treated with polyphosphoric acid (370.00 g, 3.4 mol) and heated at reflux for 5 h. The reaction mixture was concentrated in vacuo diluted with water (3 L) and the extracted with EtOAc (4 L). The organic layer was washed with aq NaOH (2 L), filtered, concentrated in vacuo and purified by distillation at reduced pressure to yield (4) 7-bromo-4-fluorobenzofuran (125.00 g; Yield = 51%. bp 80 C (1 mm/Hg) as a colorless liquid which solidified at rt. 1H NMR (400 MHz, CDCl3) delta 7.67 (d, 1H, J = 2.2 Hz), 7.39 (dd, 1H J = 5.1 & 3.7 Hz), 6.94 (d, 1H, J = 2.2 Hz), 6.86 (t, 1H, J = 8.8 Hz). |
Tags: 253429-18-4 synthesis path| 253429-18-4 SDS| 253429-18-4 COA| 253429-18-4 purity| 253429-18-4 application| 253429-18-4 NMR| 253429-18-4 COA| 253429-18-4 structure
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H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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