2-(5-Bromo-2-fluorophenyl)acetonitrile

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-Bromo-2-fluorobenzyl bromide (8.0 g, 0.03 mole) was dissolved in 1,4-Dioxane (60 mL) and added to a solution of KCN (2.04 g, 0.031 mole) in H2O (20 mL) and ethanol ( 20 mL). The resulting mixture was heated under reflux for 5 h. After cooling to rt, the product was extracted with ether ( 200 mL), washed with brine, dried over MgSO4, concentrated. Crystallized from ether/hexane to give 5-bromo-2-fluorophenylacetonitrile as a white crystalline material (5.6 g, 88%): mp 55-58° C.; 1H NMR (DMSO-d6) □4.07 ( s, 2H), 7.29( t, 1H,J=9.23 Hz), 7.60-7.69( m, 2H); MS(EI) M+. m/z 213 ; Anal. Calc. For C8H5Br2FN: C, 44.89, H, 2.35, N, 6.54. Found: C, 44.90, H, 2.24, N, 6.43. The resulting mixture was heated under reflux for 5 h the product was extracted with ether ( 200 mL) washed with brine dried over MgSO4 concentrated Crystallized from ether/hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (5-Bromo-2-fluoro-phenyl)-acetonitrile (0.5 g, 2.3 mmol) was treated with acetic acid (2 mL) and sulfuric acid (2 mL) in H2O (2 mL) at 95° C. for 5 hours. Aqueous worked-up afforded the title compound.

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Bromo-2-bromomethyl-1-fluoro-benzene (1.2 g, 3.7 mmol) and sodium cyanide (2.0 g, 4.1 mmol) were combined in DMSO (15 mL) and stirred at 90° C. for 2 hours. Once no starting material was seen by analytical tlc, the mixture was worked-up with EtOAc and H2O to give the title compound.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-Bromo-2-fluorobenzyl bromide (8.0 g, 0.03 mole) was dissolved in 1,4-Dioxane (60 mL) and added to a solution of KCN (2.04 g, 0.031 mole) in H2O (20 mL) and ethanol ( 20 mL). The resulting mixture was heated under reflux for 5 h. After cooling to rt, the product was extracted with ether ( 200 mL), washed with brine, dried over MgSO4, concentrated. Crystallized from ether/hexane to give 5-bromo-2-fluorophenylacetonitrile as a white crystalline material (5.6 g, 88%): mp 55-58° C.; 1H NMR (DMSO-d6) □4.07 ( s, 2H), 7.29( t, 1H,J=9.23 Hz), 7.60-7.69( m, 2H); MS(EI) M+. m/z 213 ; Anal. Calc. For C8H5Br2FN: C, 44.89, H, 2.35, N, 6.54. Found: C, 44.90, H, 2.24, N, 6.43. The resulting mixture was heated under reflux for 5 h the product was extracted with ether ( 200 mL) washed with brine dried over MgSO4 concentrated Crystallized from ether/hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-Bromo-2-fluorobenzyl bromide (8.0 g, 0.03 mole) was dissolved in 1,4-Dioxane (60 mL) and added to a solution of KCN (2.04 g, 0.031 mole) in H2O (20 mL) and ethanol ( 20 mL). The resulting mixture was heated under reflux for 5 h. After cooling to rt, the product was extracted with ether ( 200 mL), washed with brine, dried over MgSO4, concentrated. Crystallized from ether/hexane to give 5-bromo-2-fluorophenylacetonitrile as a white crystalline material (5.6 g, 88%): mp 55-58° C.; 1H NMR (DMSO-d6) □4.07 ( s, 2H), 7.29( t, 1H,J=9.23 Hz), 7.60-7.69( m, 2H); MS(EI) M+. m/z 213 ; Anal. Calc. For C8H5Br2FN: C, 44.89, H, 2.35, N, 6.54. Found: C, 44.90, H, 2.24, N, 6.43. The resulting mixture was heated under reflux for 5 h the product was extracted with ether ( 200 mL) washed with brine dried over MgSO4 concentrated Crystallized from ether/hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-Bromo-2-fluorobenzyl bromide (8.0 g, 0.03 mole) was dissolved in 1,4-Dioxane (60 mL) and added to a solution of KCN (2.04 g, 0.031 mole) in H2O (20 mL) and ethanol (20 mL). The resulting mixture was heated under reflux for 5 h. After cooling to rt, the product was extracted with ether (200 mL), washed with brine, dried over MgSO4, concentrated, and crystallized from ether/hexane to give 5-bromo-2-fluorophenylacetonitrile as a white crystalline material (5.6 g, 88%): mp 55-58° C.; 1H NMR (DMSO-d6) δ 4.07 (s, 2H), 7.29 (t, 1H, J=9.23 Hz), 7.60-7.69 (m, 2H); MS(EI) M+. m/z 213; Anal. Calc. For C8H5Br2FN: C, 44.89; H, 2.35; N, 6.54. Found: C, 44.90; H, 2.24; N, 6.43. The resulting mixture was heated under reflux for 5 h the product was extracted with ether (200 mL) washed with brine dried over MgSO4 concentrated crystallized from ether/hexane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-Bromo-2-fluorobenzyl bromide (8.0 g, 0.03 mole) was dissolved in 1,4-Dioxane (60 mL) and added to a solution of KCN (2.04 g, 0.031 mole) in H2O (20 mL) and ethanol (20 mL). The resulting mixture was heated under reflux for 5 h. After cooling to rt, the product was extracted with ether (200 mL), washed with brine, dried over MgSO4, concentrated, and crystallized from ether/hexane to give 5-bromo-2-fluorophenylacetonitrile as a white crystalline material (5.6 g, 88%): mp 55-58° C.; 1H NMR (DMSO-d6) δ 4.07 (s, 2H), 7.29 (t, 1H, J=9.23 Hz), 7.60-7.69 (m, 2H); MS(EI) M+. m/z 213; Anal. Calc. For C8H5Br2FN: C, 44.89; H, 2.35; N, 6.54. Found: C, 44.90; H, 2.24; N, 6.43. The resulting mixture was heated under reflux for 5 h the product was extracted with ether (200 mL) washed with brine dried over MgSO4 concentrated crystallized from ether/hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-Bromo-2-fluorobenzyl bromide (8.0 g, 0.03 mole) was dissolved in 1,4-Dioxane (60 mL) and added to a solution of KCN (2.04 g, 0.031 mole) in H2O (20 mL) and ethanol (20 mL). The resulting mixture was heated under reflux for 5 h. After cooling to rt, the product was extracted with ether (200 mL), washed with brine, dried over MgSO4, concentrated. Crystallized from ether/hexane to give 5-bromo-2-fluorophenylacetonitrile as a white crystalline material (5.6 g, 88%): mp 55-58° C.; 1H NMR (DMSO-d6) δ4.07 (s, 2H), 7.29 (t, 1H, J=9.23 Hz), 7.60-7.69 (m, 2H); MS (EI) M+. m/z 213; Anal. Calc. For C8H5Br2FN: C, 44.89; H, 2.35; N, 6.54. Found: C, 44.90; H, 2.24; N, 6.43. The resulting mixture was heated under reflux for 5 h the product was extracted with ether (200 mL) washed with brine dried over MgSO4 concentrated Crystallized from ether/hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (5-Bromo-2-fluoro-phenyl)-acetonitrile (0.5 g, 2.3 mmol) was treated with acetic acid (2 mL) and sulfuric acid (2 mL) in H2O (2 mL) at 95° C. for 5 hours. Aqueous worked-up afforded the title compound.

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Bromo-2-bromomethyl-1-fluoro-benzene (1.2 g, 3.7 mmol) and sodium cyanide (2.0 g, 4.1 mmol) were combined in DMSO (15 mL) and stirred at 90° C. for 2 hours. Once no starting material was seen by analytical tlc, the mixture was worked-up with EtOAc and H2O to give the title compound.