No renderable structure data available
C1=CC(=C(C=C1C(=O)Cl)Br)ClChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 3-bromo-4-chlorobenzoyl chloride |
|---|---|
| IUPAC Name | — |
| CAS Number | 21900-34-5 |
| Database ID | 20229730 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
3-bromo-4-chlorobenzoyl chloride (CAS 21900-34-5) 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 20229730
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-95994493296b4e6dbfe543d57d667e70Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-2af5b902dd944a6f8f25d5cc5e5b2fb1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Bromo-4-chloro-N-(2-fluoro-3-(trifluoromethyl)phenyl)benzamide was synthesized from 2-fluoro-3-(trifluromethyl)aniline and 3-bromo-4-chlorobenzoyl chloride according to the procedure described in Example 183. 3-Bromo-4-chloro-N-(2-fluoro-3-(trifluoromethyl)phenyl)benzamide was obtained as a red-orange solid. MS (M−H+) 393.9; Calc'd for C14H7BrClF4NO: 395.
Source ID: ord-ae10da11e87e4b10a4c215a42ce4aaf4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Bromo-4-chlorobenzoyl chloride was prepared from 3-bromo-4-chlorobenzoic acid according to the procedure described in Example 183 for the synthesis of 3-bromo-4-fluorobenzoyl chloride.
Source ID: ord-4bb4eefb1478471f99cf6ba765c732b9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Bromo-4-chlorobenzoyl chloride was prepared from 3-bromo-4-chlorobenzoic acid according to the procedure described in Example 183 for the synthesis of 3-bromo-4-fluorobenzoyl chloride.
Source ID: ord-4bb4eefb1478471f99cf6ba765c732b9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Bromo-4-chloro-benzoyl chloride (Step 2A, 106.9 mmol) in acetonitrile (300 mL) was added dropwise over 30 minutes to a vigorously stirring solution of 2-methylamino-phenol (15.1 g, 122.9 mmol) and NaHCO3 (18.0 g, 213.7 mmol) in acetonitrile (200 mL) and water (200 mL). The mixture was stirred for additional 1 h and then concentrated to remove acetonitrile. The solid was filtered, washed with HCl (1N, 600 mL) and water (500 mL), and dried. The solid was dissolved in dichloromethane (500 mL) and n-butylamine (20 mL) was added. The mixture was stirred at rt for 16 hrs and concentrated. The residue was partially purified via silica gel flash chromatography (eluting with 20% to 35% ethyl acetate in hexane) and then crystallized from hexane/ethyl acetate (75/25) to give 3-bromo-4-chloro-N-(2-hydroxy-phenyl)-N-methyl-benzamide (20.5 g) as a white solid. MS [M+H]+: 339.7/341.8; tR=2.19 min. (method 1) concentrated to remove acetonitrile The solid was filtered washed with HCl (1N, 600 mL) and water (500 mL) dried The solid was dissolved in dichloromethane (500 mL) n-butylamine (20 mL) was added The mixture was stirred at rt for 16 hrs concentrated The residue was partially purified via silica gel flash chromatography (eluting with 20% to 35% ethyl acetate in hexane) crystallized from hexane/ethyl acetate (75/25)
Source ID: ord-f0ac2d26e8a7401cba990c6c9581fa1eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To 3-bromo-4-chloro-benzoyl chloride (1.09 g, 4.3 mmol) in DCM (30 mL) cooled with an ice bath, was added 4-(2-amino-phenyl)-butyric acid methyl ester (0.85 g, 4.4 mmol), followed by addition of diisopropylethylamine (1 mL, 5.6 mmol) slowly. Upon the completion of the addition, ice bath was removed and the mixture was stirred at room temperature for 12 hrs. The mixture was further diluted with DCM, washed with saturated NaHCO3, 1N HCl, brine and dried over Na2SO4 and concentrated to yield 4-[2-(3-bromo-4-chloro-benzoylamino)-phenyl]-butyric acid methyl ester (1.8 g). MS [M+H]+: 411.7; tR=2.45 min. (method 1) Upon the completion of the addition, ice bath was removed The mixture was further diluted with DCM washed with saturated NaHCO3, 1N HCl, brine dried over Na2SO4 concentrated
Source ID: ord-f66f497a128842dda494a4970bd343abConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To 3-bromo-4-chloro-benzoyl chloride (1.09 g, 4.3 mmol) in DCM (30 mL) cooled with an ice bath, was added 4-(2-amino-phenyl)-butyric acid methyl ester (0.85 g, 4.4 mmol), followed by addition of diisopropylethylamine (1 mL, 5.6 mmol) slowly. Upon the completion of the addition, ice bath was removed and the mixture was stirred at room temperature for 12 hrs. The mixture was further diluted with DCM, washed with saturated NaHCO3, 1N HCl, brine and dried over Na2SO4 and concentrated to yield 4-[2-(3-bromo-4-chloro-benzoylamino)-phenyl]-butyric acid methyl ester (1.8 g). MS [M+H]+: 411.7; tR=2.45 min. (method 1) Upon the completion of the addition, ice bath was removed The mixture was further diluted with DCM washed with saturated NaHCO3, 1N HCl, brine dried over Na2SO4 concentrated
Source ID: ord-f66f497a128842dda494a4970bd343abConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-Amino-m-cresol (4.9 g, 40 mmol) was dissolved in a mixture of acetonitrile (90 mL) and water (80 mL) containing NaHCO3 (6.7 g, 80 mmol) with vigorous stirring. 3-Bromo-4-chloro-benzoyl chloride (10.1 g, 40 mmol, Step 2A) was added in several portions and the mixture was stirred at room temperature for 3 hrs. The resulting precipitates were filtered, washed with water and tert-butyl methyl ether, then dried to yield 3-bromo-4-chloro-N-(2-hydroxy-6-methyl-phenyl)-benzamide (11.3 g). MS (M+H)+: 339.7/341.7; tR=2.36 min. (method 1) The resulting precipitates were filtered washed with water and tert-butyl methyl ether dried
Source ID: ord-674ef4c8cd0b434c997b6db4addceaecConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-Amino-m-cresol (4.9 g, 40 mmol) was dissolved in a mixture of acetonitrile (90 mL) and water (80 mL) containing NaHCO3 (6.7 g, 80 mmol) with vigorous stirring. 3-Bromo-4-chloro-benzoyl chloride (10.1 g, 40 mmol, Step 2A) was added in several portions and the mixture was stirred at room temperature for 3 hrs. The resulting precipitates were filtered, washed with water and tert-butyl methyl ether, then dried to yield 3-bromo-4-chloro-N-(2-hydroxy-6-methyl-phenyl)-benzamide (11.3 g). MS (M+H)+: 339.7/341.7; tR=2.36 min. (method 1) The resulting precipitates were filtered washed with water and tert-butyl methyl ether dried
Source ID: ord-674ef4c8cd0b434c997b6db4addceaecConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Bromo-4-chloro-benzoyl chloride in DCM (200 mL) was cooled in an ice bath and triethylamine (11.1 mol, 80 mmol) was added slowly, followed by the drop-wise addition of o-anisidine (4.5 mL, 40 mmol) in DCM (50 mL). At this time the ice bath was removed and the mixture was stirred for 12 hrs, followed by partition between DCM and water. The organic layer was washed with 1 N HCl, saturated NaHCO3, brine and dried over MgSO4. Concentration of the filtrate yielded 3-bromo-4-chloro-N-(2-methoxy-phenyl)-benzamide as a pinkish solid (13.5 g). At this time the ice bath was removed by partition between DCM and water The organic layer was washed with 1 N HCl, saturated NaHCO3, brine dried over MgSO4
Source ID: ord-781ac925a311408b93f84f32f8195628Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To 3-bromo-4-chloro-benzoic acid (9.4 g, 40 mmol) in dry DCM (100 mL), was added DMF (0.5 mL) followed by addition of oxalyl chloride (22.5 mL, 55 mmol, 2M in DCM) slowly. The mixture was stirred for 1 hr, then concentrated to yield 3-bromo-4-chloro-benzoyl chloride as an off-white solid. concentrated
Source ID: ord-8e24efe67aea44ecaa63baa40ff628baPubChem References
These sources are listed in the compound's public database record.
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