2-(3-fluoro-5-methoxyphenyl)acetonitrile

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(3-fluoro-5-methoxyphenyl)acetonitrile (2.62 g, 16 mmol) in MeOH:H2O (1:1; 15 mL), NaOH (1.28 g, 32 mmol) was added. Then the mixture was stirred at 65° C. for 4 h. The mixture was cooled to room temperature, and 4M aqueous HCl solution was added until the pH was adjusted to 4-5. The mixture was filtered and the solid obtained was washed with H2O (2×5 mL) to give 2.33 g of 2-(3-fluoro-5-methoxyphenyl)acetic acid. 1H NMR (CDCl3): δ 6.52-6.62 (m, 3H), 3.78 (s, 3H), 3.59 (s, 2H). The mixture was cooled to room temperature The mixture was filtered the solid obtained was washed with H2O (2×5 mL)

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-(chloromethyl)-3-fluoro-5-methoxybenzene (2.9 g, 17 mmol) in DMSO (20 mL), a solution of KCN (2.2 g, 34 mmol) and KI (5.6 g, 34 mmol) in H2O (10 mL) was added. The mixture was stirred at 45° C. for 6 h, poured into H2O (20 mL), and extracted with DCM (3×30 mL). The organic phase was washed with brine (2×10 mL), dried over Na2SO4, and concentrated to give 2.62 g of 2-(3-fluoro-5-methoxyphenyl)acetonitrile. 1H NMR (CDCl3): δ 6.62-6.68 (m, 2H), 6.56-6.60 (m, 1H), 3.80 (s, 3H), 3.70 (s, 2H). extracted with DCM (3×30 mL) The organic phase was washed with brine (2×10 mL) dried over Na2SO4 concentrated

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(3-fluoro-5-methoxyphenyl)acetonitrile (2.62 g, 16 mmol) in MeOH:H2O (1:1; 15 mL), NaOH (1.28 g, 32 mmol) was added. Then the mixture was stirred at 65° C. for 4 h. The mixture was cooled to room temperature, and 4M aqueous HCl solution was added until the pH was adjusted to 4˜5. The mixture was filtered and the solid obtained was washed with H2O (2×5 mL) to give 2.33 g of 2-(3-fluoro-5-methoxyphenyl)acetic acid. 1H NMR (CDCl3): δ 6.52-6.62 (m, 3H), 3.78 (s, 3H), 3.59 (s, 2H). The mixture was cooled to room temperature The mixture was filtered the solid obtained was washed with H2O (2×5 mL)

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-(chloromethyl)-3-fluoro-5-methoxybenzene (2.9 g, 17 mmol) in DMSO (20 mL), a solution of KCN (2.2 g, 34 mmol) and KI (5.6 g, 34 mmol) in H2O (10 mL) was added. The mixture was stirred at 45° C. for 6 h, poured into H2O (20 mL), and extracted with DCM (3×30 mL). The organic phase was washed with brine (2×10 mL), dried over Na2SO4, and concentrated to give 2.62 g of 2-(3-fluoro-5-methoxyphenyl)acetonitrile. 1H NMR (CDCl3): δ 6.62-6.68 (m, 2H), 6.56-6.60 (m, 1H), 3.80 (s, 3H), 3.70 (s, 2H). extracted with DCM (3×30 mL) The organic phase was washed with brine (2×10 mL) dried over Na2SO4 concentrated