No renderable structure data available
C1=CC(=C(C=C1C(=O)CBr)Cl)FChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2-bromo-1-(3-chloro-4-fluorophenyl)ethanone |
|---|---|
| IUPAC Name | — |
| CAS Number | 63529-30-6 |
| Database ID | 2782785 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2-bromo-1-(3-chloro-4-fluorophenyl)ethanone (CAS 63529-30-6) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 2782785
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
11 reactions · 11 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-3a302407e2874961be43d462885bb246Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Dissolve 1-benzyl-piperidine-4-carboxamidine dihydrochloride (2 g; 1.00 equiv; 6.89 mmoles) in dimethylformamide (90 mL). Add powdered potassium carbonate (4 equiv; 27.56 mmoles; 3.8095 g) and warm to ˜45° C. Add 3-chloro-4-fluoro-phenacyl bromide (2.00 equiv; 13.782 mmoles; 3.5366 g) in 8 mL with DMF dropwise over 40 minutes. Dilute with 50 mL ethyl acetate, stir 5 min and filter. Evaporate and partition with ethyl acetate/sat. sodium bicarbonate, wash organic layer with water, then saturated aqueous sodium chloride. Dry with MgSO4, filter and evaporate to red foam. Purify over flash silica gel with 0-10% MeOH/ACN. Pool fractions to give 1.9772 g (5.346 mmol, 78%) 1-Benzyl-4-[5-(3-chloro-4-fluoro-phenyl)-1H-imidazol-2-yl]-piperidine. filter Evaporate partition with ethyl acetate/ sodium bicarbonate, wash organic layer with water Dry with MgSO4 filter evaporate to red foam Purify over flash silica gel with 0-10% MeOH/ACN
Source ID: ord-b2e0556a4b61428b852846c57bac4a2bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a flame-dried flask was added 2-(4-isopropyl-piperazin-1-yl)-isonicotinonitrile (1.09 g, 4.75 mmol) and anhydrous THF (5 ml). To this stirred solution under nitrogen atmosphere was added a 1.0 M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (4.75 ml, 1.0 equiv) via syringe. The reaction mixture was stirred at room temperature for 3 hours. Saturated aqueous sodium bicarbonate solution (7.78 ml) was added, followed by water (7.8 ml), K2CO3 (0.59 g, 4.27 mmol, 0.9 equiv), and a solution of 2-bromo-3′-chloro-4′-fluoroacetophenone (1.19 g, 4.75 mmol, 1.0 equiv) in chloroform (20 ml). After stirring overnight, the aqueous phase was separated and extracted with chloroform. The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was dissolved in glacial acetic acid (10 ml) and heated to 50° C. for 1 hour. The mixture was cooled to room temperature and partitioned between aqueous 1N NaOH solution and ethyl acetate. The organic phase was removed, and the aqueous phase was saturated with NaCl and extracted again with ethyl acetate. The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Purification of the residue by flash column chromatography (CH2Cl2 grading to 10% methanol/0.5% ammonium hydroxide/CH2Cl2) provided the desired product, which was converted to its hydrochloride salt (MeOH/ethereal HCl; 0.92 g). MS m/z 400 (M++1). After stirring overnight the aqueous phase was separated extracted with chloroform dried over anhydrous magnesium sulfate filtered concentrated in vacuo The residue was dissolved in glacial acetic acid (10 ml) heated to 50° C. for 1 hour The mixture was cooled to room temperature partitioned between aqueous 1N NaOH solution and ethyl acetate The organic phase was removed extracted again with ethyl acetate dried over anhydrous magnesium sulfate filtered concentrated in vacuo Purification of the residue by flash column chromatography (CH2Cl2 grading to 10% methanol/0.5% ammonium hydroxide/CH2Cl2)
Source ID: ord-c9a37085e78e48368e76c676d9ebc41fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of (R)—((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate (diastereomer 1 of I2) (75 mg, 0.22 mmol) in EtOAc (5 ml), was added 2-bromo-1-(3-chloro-4-fluorophenyl)ethanone (61.7 mg, 0.24 mmol), and the reaction was stirred at room temperature for 15 hours. The precipitate was collected by suction filtration to obtain (R)-1-(2-(3-chloro-4-fluorophenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (120.3 mg, 92% yield). The precipitate was collected by suction filtration
Source ID: ord-d6852931e90c4cdb87567321710e36daConditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Dissolve 1-benzyl-piperidine-4-carboxamidine dihydrochloride (2 g; 1.00 equiv; 6.89 mmoles) in dimethylformamide (90 mL). Add powdered potassium carbonate (4 equiv; 27.56 mmoles; 3.8095 g) and warm to ˜45° C. Add 3-chloro-4-fluoro-phenacyl bromide (2.00 equiv; 13.782 mmoles; 3.5366 g) in 8 mL with DMF dropwise over 40 minutes. Dilute with 50 mL ethyl acetate, stir 5 min and filter. Evaporate and partition with ethyl acetate/sat. sodium bicarbonate, wash organic layer with water, then saturated aqueous sodium chloride. Dry with MgSO4, filter and evaporate to red foam. Purify over flash silica gel with 0-10% MeOH/ACN. Pool fractions to give 1.9772 g (5.346 mmol, 78%) 1-Benzyl-4-[5-(3-chloro-4-fluoro-phenyl)-1H-imidazol-2-yl]-piperidine. filter Evaporate partition with ethyl acetate/ sodium bicarbonate, wash organic layer with water Dry with MgSO4 filter evaporate to red foam Purify over flash silica gel with 0-10% MeOH/ACN
Source ID: ord-b2e0556a4b61428b852846c57bac4a2bConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-3a302407e2874961be43d462885bb246Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1.35 g of the compound from Example 1A having a purity of 68% (5.37 mmol) are heated under reflux in 25 ml of ethanol, a solution of 0.72 g (5.37 mmol) of ethyl amino(thioxo)acetate and 10 ml of ethanol is added dropwise and the mixture is heated under reflux for 18 hours. The reaction mixture is concentrated and the residue is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 10:1), and 1.94 g of the title compound having a purity of 57% (100% of theory) are obtained. are heated the mixture is heated under reflux for 18 hours The reaction mixture is concentrated the residue is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 10:1), and 1.94 g of the title compound are obtained
Source ID: ord-7dbe9f8e65c546799279de297ac7ce8dConditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-Bromo-3′-chloro-4′-fluoroacetophenone (available from Aldrich Chemical Company, Inc.; 80.5 mg, 0.32 mmol) was added to a solution of 2′-nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester (which may be prepared as described for Intermediate 4; 100 mg, 0.32 mmol) in THF (2 mL), and the resulting mixture was stirred at 40° C. for 20 h. The reaction mixture was evaporated to dryness and the residue was stirred with ethanol (5 mL). The precipitate was collected by filtration (100 mg) and used directly in the next step without purification. The reaction mixture was evaporated to dryness the residue was stirred with ethanol (5 mL) The precipitate was collected by filtration (100 mg) used directly in the next step without purification
Source ID: ord-032f764b273d4e42ab468111fd59258bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a flame-dried flask was added 2-(4-isopropyl-piperazin-1-yl)-isonicotinonitrile (1.09 g, 4.75 mmol) and anhydrous THF (5 ml). To this stirred solution under nitrogen atmosphere was added a 1.0 M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (4.75 ml, 1.0 equiv) via syringe. The reaction mixture was stirred at room temperature for 3 hours. Saturated aqueous sodium bicarbonate solution (7.78 ml) was added, followed by water (7.8 ml), K2CO3 (0.59 g, 4.27 mmol, 0.9 equiv), and a solution of 2-bromo-3′-chloro-4′-fluoroacetophenone (1.19 g, 4.75 mmol, 1.0 equiv) in chloroform (20 ml). After stirring overnight, the aqueous phase was separated and extracted with chloroform. The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was dissolved in glacial acetic acid (10 ml) and heated to 50° C. for 1 hour. The mixture was cooled to room temperature and partitioned between aqueous 1N NaOH solution and ethyl acetate. The organic phase was removed, and the aqueous phase was saturated with NaCl and extracted again with ethyl acetate. The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Purification of the residue by flash column chromatography (CH2Cl2 grading to 10% methanol/0.5% ammonium hydroxide/CH2Cl2) provided the desired product, which was converted to its hydrochloride salt (MeOH/ethereal HCl; 0.92 g). MS m/z 400 (M++1). After stirring overnight the aqueous phase was separated extracted with chloroform dried over anhydrous magnesium sulfate filtered concentrated in vacuo The residue was dissolved in glacial acetic acid (10 ml) heated to 50° C. for 1 hour The mixture was cooled to room temperature partitioned between aqueous 1N NaOH solution and ethyl acetate The organic phase was removed extracted again with ethyl acetate dried over anhydrous magnesium sulfate filtered concentrated in vacuo Purification of the residue by flash column chromatography (CH2Cl2 grading to 10% methanol/0.5% ammonium hydroxide/CH2Cl2)
Source ID: ord-c9a37085e78e48368e76c676d9ebc41fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of (R)—((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate (diastereomer 1 of I2) (75 mg, 0.22 mmol) in EtOAc (5 ml), was added 2-bromo-1-(3-chloro-4-fluorophenyl)ethanone (61.7 mg, 0.24 mmol), and the reaction was stirred at room temperature for 15 hours. The precipitate was collected by suction filtration to obtain (R)-1-(2-(3-chloro-4-fluorophenyl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (120.3 mg, 92% yield). The precipitate was collected by suction filtration
Source ID: ord-d6852931e90c4cdb87567321710e36daConditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Dissolve 1-benzyl-piperidine-4-carboxamidine dihydrochloride (2 g; 1.00 equiv; 6.89 mmoles) in dimethylformamide (90 mL). Add powdered potassium carbonate (4 equiv; 27.56 mmoles; 3.8095 g) and warm to ˜45° C. Add 3-chloro-4-fluoro-phenacyl bromide (2.00 equiv; 13.782 mmoles; 3.5366 g) in 8 mL with DMF dropwise over 40 minutes. Dilute with 50 mL ethyl acetate, stir 5 min and filter. Evaporate and partition with ethyl acetate/sat. sodium bicarbonate, wash organic layer with water, then saturated aqueous sodium chloride. Dry with MgSO4, filter and evaporate to red foam. Purify over flash silica gel with 0-10% MeOH/ACN. Pool fractions to give 1.9772 g (5.346 mmol, 78%) 1-Benzyl-4-[5-(3-chloro-4-fluoro-phenyl)-1H-imidazol-2-yl]-piperidine. filter Evaporate partition with ethyl acetate/ sodium bicarbonate, wash organic layer with water Dry with MgSO4 filter evaporate to red foam Purify over flash silica gel with 0-10% MeOH/ACN
Source ID: ord-b2e0556a4b61428b852846c57bac4a2bPubChem References
These sources are listed in the compound's public database record.
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