Sodium Iodide → 4-Iodophenylacetonitrile

Temperature

110 °C

A round bottomed flask fitted with a magnetic stirrer was charged with 1.22 g of copper iodide (Sigma Aldrich), 25 g of 4-bromophenylacetonitrile (Apollo Scientific) and 38.37 g of sodium iodide (Sigma Aldrich) under argon. The round bottomed flask was evacuated and backfilled with argon three times. N,N′-Dimethylethylenediamine (1.38 mL, Sigma Aldrich) and 25 mL dioxane were added and the mixture was heated to 110° C. for 2 hours (h). The reaction was allowed to cool to room temperature (rt) and 125 mL of 30% aqueous ammonia was added. The mixture was then poured onto 500 mL water and extracted three times with dichloromethane (DCM) and the combined organics dried over MgSO4. The solvent was removed under reduced pressure to afford the title compound as brown oil that solidified on standing. Yield: 29.97 g. 1H NMR (400 MHz, CDCl3), δ 7.71 (2H, d, Ar—H), 7.08 (2H, d, Ar—H), 3.66 (2H, s, CH2).

1. customA round bottomed flask fitted with a magnetic stirrer
2. customThe round bottomed flask was evacuated
3. additionN,N′-Dimethylethylenediamine (1.38 mL, Sigma Aldrich) and 25 mL dioxane were added
4. temperatureto cool to room temperature (rt) and 125 mL of 30% aqueous ammonia
5. additionwas added
6. additionThe mixture was then poured onto 500 mL water
7. extractionextracted three times with dichloromethane (DCM)
8. dry with materialthe combined organics dried over MgSO4
9. customThe solvent was removed under reduced pressure

ORD record

ord-1a632184d8984e0aa09b9d2f85005676

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09431145B2