No renderable structure data available
C1=CC(=C(C(=C1)C#N)F)CBrChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 3-(bromomethyl)-2-fluorobenzonitrile |
|---|---|
| IUPAC Name | — |
| CAS Number | 1246527-18-3 |
| Database ID | 66678465 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
3-(bromomethyl)-2-fluorobenzonitrile (CAS 1246527-18-3) 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 66678465
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-d02b8f20d86d48b9a1c5c2ef5d1db0afConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-6425ae5d07b646cf81b80bcb8acc66f0Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 2-fluoro-3-methylbenzonitrile (200 mg, 1.5 mmol) in 1,2-dichloroethane (30 ml) was added NBS (266 mg, 1.49 mmol) and AIBN (29 mg, 0.15 mmol) at RT. The reaction mixture was then heated to 80° C., and the reaction mixture was stirred for 2 h. After complete consumption of the starting material (by TLC), the reaction mixture was cooled to RT. The volatiles were removed under reduced pressure to obtain the crude material. Purification by silica gel column chromatography eluting with 2-3% EtOAc/hexane afforded compound I-6 (250 mg, 1.15 mmol, 78%) as colorless liquid. 1H NMR (500 MHz, CDCl3): δ 7.69-7.65 (m, 1H), 7.62-7.58 (m, 1H), 7.28-7.25 (m, 1H), 4.50 (s, 2H). After complete consumption of the starting material (by TLC) the reaction mixture was cooled to RT The volatiles were removed under reduced pressure
Source ID: ord-e3c7dd3f39684600ae0a99cba126c010Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-(Bromomethyl)-2-fluorobenzonitrile (Intermediate 84, 1.39 g, 6.49 mmol) was dissolved in MeOH (10 mL) and sodium methoxide (1.238 mL, 6.49 mmol) was added. The mixture was stirred at r.t. for 2 h. This mixture was concentrated and then partitioned between water and EtOAc. The organic layer was separated and then concentrated in vacuo. The resulting residue was purified by flash chromatography using EtOAc/heptanes as eluent to give the title compound (0.900 g, 84% yield): 1H NMR (500 MHz, DMSO-d6) δ ppm 3.32 (s, 3 H) 4.52 (br. s, 2 H) 7.42 (t, 1 H) 7.77-7.84 (m, 1 H) 7.86-7.92 (m, 1 H); MS (EI) m/z 166 M+. This mixture was concentrated partitioned between water and EtOAc The organic layer was separated concentrated in vacuo The resulting residue was purified by flash chromatography
Source ID: ord-94cb9fe8f54c42e09c159ae346d084e9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: NBS (1.729 g, 9.71 mmol) was added to a solution of 2-fluoro-3-methylbenzonitrile (1.25 g, 9.25 mmol) in acetonitrile (25 mL). The obtained mixture was refluxed, and then benzoic peroxyanhydride (0.045 g, 0.18 mmol) was added. The reaction mixture was refluxed overnight, then cooled to r.t. and water was added. The aqueous phase was discarded and the organic phase was dried over MgSO4 and concentrated. The crude product was purified by flash chromatography using a gradient of EtOAc in heptane as eluent to give the title compound (1.39 g, 70% yield): 1H NMR (500 MHz, DMSO-d6) δ ppm 4.75 (s, 2 H) 7.43 (t, 1 H) 7.93 (t, 2 H); MS (EI) m/z 213 M+. The obtained mixture was refluxed The reaction mixture was refluxed overnight the organic phase was dried over MgSO4 concentrated The crude product was purified by flash chromatography
Source ID: ord-09034a4e7e1e4757b50e413998ec2978Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 2-fluoro-3-methylbenzonitrile (200 mg, 1.5 mmol) in 1,2-dichloroethane (30 ml) was added NBS (266 mg, 1.49 mmol) and AIBN (29 mg, 0.15 mmol) at RT. The reaction mixture was then heated to 80° C., and the reaction mixture was stirred for 2 h. After complete consumption of the starting material (by TLC), the reaction mixture was cooled to RT. The volatiles were removed under reduced pressure to obtain the crude material. Purification by silica gel column chromatography eluting with 2-3% EtOAc/hexane afforded compound I-6 (250 mg, 1.15 mmol, 78%) as colorless liquid. 1H NMR (500 MHz, CDCl3): δ 7.69-7.65 (m, 1H), 7.62-7.58 (m, 1H), 7.28-7.25 (m, 1H), 4.50 (s, 2H). After complete consumption of the starting material (by TLC) the reaction mixture was cooled to RT The volatiles were removed under reduced pressure
Source ID: ord-e3c7dd3f39684600ae0a99cba126c010Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 2-fluoro-3-methylbenzonitrile (200 mg, 1.5 mmol) in 1,2-dichloroethane (30 ml) was added NBS (266 mg, 1.49 mmol) and AIBN (29 mg, 0.15 mmol) at RT. The reaction mixture was then heated to 80° C., and the reaction mixture was stirred for 2 h. After complete consumption of the starting material (by TLC), the reaction mixture was cooled to RT. The volatiles were removed under reduced pressure to obtain the crude material. Purification by silica gel column chromatography eluting with 2-3% EtOAc/hexane afforded compound I-6 (250 mg, 1.15 mmol, 78%) as colorless liquid. 1H NMR (500 MHz, CDCl3): δ 7.69-7.65 (m, 1H), 7.62-7.58 (m, 1H), 7.28-7.25 (m, 1H), 4.50 (s, 2H). After complete consumption of the starting material (by TLC) the reaction mixture was cooled to RT The volatiles were removed under reduced pressure
Source ID: ord-e3c7dd3f39684600ae0a99cba126c010Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-6425ae5d07b646cf81b80bcb8acc66f0Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 2-fluoro-3-methylbenzonitrile (200 mg, 1.5 mmol) in 1,2-dichloroethane (30 ml) was added NBS (266 mg, 1.49 mmol) and AIBN (29 mg, 0.15 mmol) at RT. The reaction mixture was then heated to 80° C., and the reaction mixture was stirred for 2 h. After complete consumption of the starting material (by TLC), the reaction mixture was cooled to RT. The volatiles were removed under reduced pressure to obtain the crude material. Purification by silica gel column chromatography eluting with 2-3% EtOAc/hexane afforded compound I-6 (250 mg, 1.15 mmol, 78%) as colorless liquid. 1H NMR (500 MHz, CDCl3): δ 7.69-7.65 (m, 1H), 7.62-7.58 (m, 1H), 7.28-7.25 (m, 1H), 4.50 (s, 2H). After complete consumption of the starting material (by TLC) the reaction mixture was cooled to RT The volatiles were removed under reduced pressure
Source ID: ord-e161c0751dcc4d6ab09491ac4725617bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-(Bromomethyl)-2-fluorobenzonitrile (Intermediate 84, 1.39 g, 6.49 mmol) was dissolved in MeOH (10 mL) and sodium methoxide (1.238 mL, 6.49 mmol) was added. The mixture was stirred at r.t. for 2 h. This mixture was concentrated and then partitioned between water and EtOAc. The organic layer was separated and then concentrated in vacuo. The resulting residue was purified by flash chromatography using EtOAc/heptanes as eluent to give the title compound (0.900 g, 84% yield): 1H NMR (500 MHz, DMSO-d6) δ ppm 3.32 (s, 3 H) 4.52 (br. s, 2 H) 7.42 (t, 1 H) 7.77-7.84 (m, 1 H) 7.86-7.92 (m, 1 H); MS (EI) m/z 166 M+. This mixture was concentrated partitioned between water and EtOAc The organic layer was separated concentrated in vacuo The resulting residue was purified by flash chromatography
Source ID: ord-b4c74e7765de4388bac7316b80399f9fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: NBS (1.729 g, 9.71 mmol) was added to a solution of 2-fluoro-3-methylbenzonitrile (1.25 g, 9.25 mmol) in acetonitrile (25 mL). The obtained mixture was refluxed, and then benzoic peroxyanhydride (0.045 g, 0.18 mmol) was added. The reaction mixture was refluxed overnight, then cooled to r.t. and water was added. The aqueous phase was discarded and the organic phase was dried over MgSO4 and concentrated. The crude product was purified by flash chromatography using a gradient of EtOAc in heptane as eluent to give the title compound (1.39 g, 70% yield): 1H NMR (500 MHz, DMSO-d6) δ ppm 4.75 (s, 2 H) 7.43 (t, 1 H) 7.93 (t, 2 H); MS (EI) m/z 213 M. The obtained mixture was refluxed The reaction mixture was refluxed overnight the organic phase was dried over MgSO4 concentrated The crude product was purified by flash chromatography
Source ID: ord-8d4c778fb0214446a2b25e395497b4a2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-(Bromomethyl)-2-fluorobenzonitrile (Intermediate 84, 1.39 g, 6.49 mmol) was dissolved in MeOH (10 mL) and sodium methoxide (1.238 mL, 6.49 mmol) was added. The mixture was stirred at r.t. for 2 h. This mixture was concentrated and then partitioned between water and EtOAc. The organic layer was separated and then concentrated in vacuo. The resulting residue was purified by flash chromatography using EtOAc/heptanes as eluent to give the title compound (0.900 g, 84% yield): 1H NMR (500 MHz, DMSO-d6) δ ppm 3.32 (s, 3H) 4.52 (br. s, 2H) 7.42 (t, 1H) 7.77-7.84 (m, 1H) 7.86-7.92 (m, 1H); MS (EI) m/z 166 M+. This mixture was concentrated partitioned between water and EtOAc The organic layer was separated concentrated in vacuo The resulting residue was purified by flash chromatography
Source ID: ord-c53f4da798ab4221aafcee0c4034e4a5PubChem References
These sources are listed in the compound's public database record.
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