5-bromo-2-(difluoromethyl)benzonitrile

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

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

Procedure: A mixture of the title compound from Example 302 Step A (2.44 g, 10.5 mmol), CCl3Br (8 mL) and Na2CO3 (480 mg, 4.5 mmol) in a sealed vessel was illuminated by a sunlamp for 30 h. Purification by silica gel flash chromatography using 8:1 to 6:1 to 4:1 hexanes:DCM as mobile phase yielded the title compound: 1H NMR (500 MHz, CD2Cl2) δ 8.03 (s, 1H), 7.92 (d, J=8.5 Hz, 1H), 7.65 (d, J=8.5 Hz, 1H). was illuminated by a sunlamp for 30 h Purification by silica gel flash chromatography

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

Procedure: A mixture of 4-bromo-1-(difluoromethyl)-2-fluorobenzene (5.0 g, 22 mmol) and KCN (4.34 g, 67 mmol) was heated at 150° C. in NMP (50 mL) for 16 h. After trituration with a mixture of water, hexane, EtOAc and DCM, the organic layer was concentrated and purified by silica gel flash chromatography using hexanes:DCM (4:1 to 4:1.5 v/v) as mobile phase to yield the title compound: 1H NMR (500 MHz, CD2Cl2) δ 7.97 (s, 1H), 7.93 (d, J=8.5 Hz, 1H), 7.67 (d, J=8.5 Hz, 1H), 6.95 (t, J=54.5 Hz, 1H). the organic layer was concentrated purified by silica gel flash chromatography