Reaction #4028863
Related Literature (1)
openreactiondata ↗doi:10.1039/C8SC04228D
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-442d997b8ad64b07b24edfdf1f668438No renderable structure data available
C1=CC(=CC=C1CBr)C(=O)BrChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-(bromomethyl)benzoyl bromide |
|---|---|
| IUPAC Name | — |
| CAS Number | 876-07-3 |
| Database ID | 4640671 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-(bromomethyl)benzoyl bromide (CAS 876-07-3) 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 4640671
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-442d997b8ad64b07b24edfdf1f668438Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-Bromomethylbenzoyl bromide (13.9 g, 50 mmol, 1.0 eq) was added to 50 mL of DCM, followed by t-butanol (9.6 mL, 100 mmol, 2.0 eq) and the mixture was slowly warmed to room temperature. After 20 hours, the reaction was concentrated under reduced pressure, dissolved into 350 mL EtOAc, washed with 400 mL sat. bicarbonate and 200 mL saturated aqueous NaCl. The organic was dried over MgSO4, filtered, and concentrated under reduced pressure to yield intermediate (19a) as a semisolid (7.3 g). the reaction was concentrated under reduced pressure dissolved into 350 mL EtOAc washed with 400 mL sat. bicarbonate and 200 mL saturated aqueous NaCl The organic was dried over MgSO4 filtered concentrated under reduced pressure
Source ID: ord-0d198f043ec84c9a9db0c7fc309d342bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-Bromomethylbenzoyl bromide (13.9 g, 50 mmol, 1.0 eq) was added to 50 mL of DCM, followed by t-butanol (9.6 mL, 100 mmol, 2.0 eq) and the mixture was slowly warmed to room temperature. After 20 hours, the reaction was concentrated under reduced pressure, dissolved into 350 mL EtOAc, washed with 400 mL sat. bicarbonate and 200 mL saturated aqueous NaCl. The organic was dried over MgSO4, filtered, and concentrated under reduced pressure to yield intermediate (19a) as a semisolid (7.3 g). the reaction was concentrated under reduced pressure dissolved into 350 mL EtOAc washed with 400 mL sat. bicarbonate and 200 mL saturated aqueous NaCl The organic was dried over MgSO4 filtered concentrated under reduced pressure
Source ID: ord-dca2709b9a38463b9b9d24df3ee55507Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-Bromomethyl-benzoyl bromide (0.70 g, 2.52 mmol) was made 0.21 M in anhydrous DCM and cooled to −78° C. To this stirring solution was added (2-amino-4-thiophen-2-yl-phenyl)-carbamic acid tert-butyl ester (0.73 g, 2.52 mmol) followed by DIPEA (0.98 g, 7.56 mmol). The resulting solution was warmed to ambient temperature and stirred for 18 hours. The reaction mixture was then diluted with 0.1 N HCl and extracted with EtOAc. The organic layer was then washed with saturated aqueous sodium bicarbonate, brine, dried (MgSO4), and concentrated in vacuo to afford the title compound: 1H NMR (DMSO-d6, 600 MHz) 9.90 (s, 1H), 8.72 (s, 1H), 7.94 (d, J=7.8. Hz, 2H), 7.78-7.80 (m, 1H), 7.57-7.62 (m, 3H), 7.47-7.51 (m, 2H), 7.42-7.44 (m, 1H), 7.09-7.12 (m, 1H), 4.77 (s, 2H), 1.43 (s, 9H). The resulting solution was warmed to ambient temperature extracted with EtOAc The organic layer was then washed with saturated aqueous sodium bicarbonate, brine dried (MgSO4) concentrated in vacuo
Source ID: ord-f5ea022b28b947cca98a473ee054d7a3Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-Bromomethylbenzoyl bromide (13.9 g, 50 mmol, 1.0 eq) was added to 50 mL of DCM, followed by t-butanol (9.6 mL, 100 mmol, 2.0 eq) and the mixture was slowly warmed to room temperature. After 20 hours, the reaction was concentrated under reduced pressure, dissolved into 350 mL EtOAc, washed with 400 mL sat. bicarbonate and 200 mL saturated aqueous NaCl. The organic was dried over MgSO4, filtered, and concentrated under reduced pressure to yield intermediate (19a) as a semisolid (7.3 g). the reaction was concentrated under reduced pressure dissolved into 350 mL EtOAc washed with 400 mL sat. bicarbonate and 200 mL saturated aqueous NaCl The organic was dried over MgSO4 filtered concentrated under reduced pressure
Source ID: ord-d4d6356c2ab94756b36d6d18cbeb3f42Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-Bromomethylbenzoyl bromide (13.9 g, 50 mmol, 1.0 eq) was added to 50 mL of DCM, followed by t-butanol (9.6 mL, 100 mmol, 2.0 eq) and the mixture was slowly warmed to room temperature. After 20 hours, the reaction was concentrated under reduced pressure, dissolved into 350 mL EtOAc, washed with 400 mL sat. bicarbonate and 200 mL saturated aqueous NaCl. The organic was dried over MgSO4, filtered, and concentrated under reduced pressure to yield intermediate (19a) as a semisolid (7.3 g). the reaction was concentrated under reduced pressure dissolved into 350 mL EtOAc washed with 400 mL sat. bicarbonate and 200 mL saturated aqueous NaCl The organic was dried over MgSO4 filtered concentrated under reduced pressure
Source ID: ord-7af61c07c1924ed583535a36191f4ca6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-Bromomethylbenzoyl bromide (13.9 g, 50 mmol, 1.0 eq) was added to 50 mL of DCM, followed by t-butanol (9.6 mL, 100 mmol, 2.0 eq) and the mixture was slowly warmed to room temperature. After 20 hours, the reaction was concentrated under reduced pressure, dissolved into 350 mL EtOAc, washed with 400 mL sat. bicarbonate and 200 mL saturated aqueous NaCl. The organic was dried over MgSO4, filtered, and concentrated under reduced pressure to yield intermediate (19a) as a semisolid (7.3 g). the reaction was concentrated under reduced pressure dissolved into 350 mL EtOAc washed with 400 mL sat. bicarbonate and 200 mL saturated aqueous NaCl The organic was dried over MgSO4 filtered concentrated under reduced pressure
Source ID: ord-7af61c07c1924ed583535a36191f4ca6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-Bromomethylbenzoyl bromide (13.9 g, 50 mmol, 1.0 eq) was added to 50 mL of DCM, followed by t-butanol (9.6 mL, 100 mmol, 2.0 eq) and the mixture was slowly warmed to room temperature. After 20 hours, the reaction was concentrated under reduced pressure, dissolved into 350 mL EtOAc, washed with 400 mL sat. bicarbonate and 200 mL saturated aqueous NaCl. The organic was dried over MgSO4, filtered, and concentrated under reduced pressure to yield intermediate (19a) as a semisolid (7.3 g). the reaction was concentrated under reduced pressure dissolved into 350 mL EtOAc washed with 400 mL sat. bicarbonate and 200 mL saturated aqueous NaCl The organic was dried over MgSO4 filtered concentrated under reduced pressure
Source ID: ord-6701658534f54ae4adbf78946dc2fd91Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-Bromomethylbenzoyl bromide (13.9 g, 50 mmol, 1.0 eq) was added to 50 mL of DCM, followed by t-butanol (9.6 mL, 100 mmol, 2.0 eq) and the mixture was slowly warmed to room temperature. After 20 hours, the reaction was concentrated under reduced pressure, dissolved into 350 mL EtOAc, washed with 400 mL sat. bicarbonate and 200 mL saturated aqueous NaCl. The organic was dried over MgSO4, filtered, and concentrated under reduced pressure to yield intermediate (19a) as a semisolid (7.3 g). the reaction was concentrated under reduced pressure dissolved into 350 mL EtOAc washed with 400 mL sat. bicarbonate and 200 mL saturated aqueous NaCl The organic was dried over MgSO4 filtered concentrated under reduced pressure
Source ID: ord-6701658534f54ae4adbf78946dc2fd91Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-Bromomethylbenzoyl bromide (13.9 g, 50 mmol, 1.0 eq) was added to 50 mL of DCM, followed by t-butanol (9.6 mL, 100 mmol, 2.0 eq) and the mixture was slowly warmed to room temperature. After 20 hours, the reaction was concentrated under reduced pressure, dissolved into 350 mL EtOAc, washed with 400 mL sat. bicarbonate and 200 mL saturated aqueous NaCl. The organic was dried over MgSO4, filtered, and concentrated under reduced pressure to yield intermediate (19a) as a semisolid (7.3 g). the reaction was concentrated under reduced pressure dissolved into 350 mL EtOAc washed with 400 mL sat. bicarbonate and 200 mL saturated aqueous NaCl The organic was dried over MgSO4 filtered concentrated under reduced pressure
Source ID: ord-0d198f043ec84c9a9db0c7fc309d342bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-Bromomethylbenzoyl bromide (13.9 g, 50 mmol, 1.0 eq) was added to 50 mL of DCM, followed by t-butanol (9.6 mL, 100 mmol, 2.0 eq) and the mixture was slowly warmed to room temperature. After 20 hours, the reaction was concentrated under reduced pressure, dissolved into 350 mL EtOAc, washed with 400 mL sat. bicarbonate and 200 mL saturated aqueous NaCl. The organic was dried over MgSO4, filtered, and concentrated under reduced pressure to yield intermediate (19a) as a semisolid (7.3 g). the reaction was concentrated under reduced pressure dissolved into 350 mL EtOAc washed with 400 mL sat. bicarbonate and 200 mL saturated aqueous NaCl The organic was dried over MgSO4 filtered concentrated under reduced pressure
Source ID: ord-0d198f043ec84c9a9db0c7fc309d342bConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-442d997b8ad64b07b24edfdf1f668438PubChem References
These sources are listed in the compound's public database record.
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