Réaction #7780

Équation de réaction

2-[3-bromo-4-(bromomethyl)phenyl]-1,3-benzoxazole

sodium cyanide

Water

→

[4-(1,3-benzoxazol-2-yl)-2-bromophenyl]acetonitrile

Solvants

DMF H2O

Conditions de réaction

Traitement

1. 1
   Extractionwas extracted with EtOAc (3×)
2. 2
   Lavagewashed with brine (2×)
3. 3
   Séchagedried over Na2SO4
4. 4
   Autreevaporated to dryness
5. 5
   Autreto give an orange oil
6. 6
   AutreThe crude oil was purified by flash chromatography
7. 7
   Lavageeluting with a gradient of EtOAc

Mode opératoire

A mixture of 2-[3-bromo-4-(bromomethyl)phenyl]-1,3-benzoxazole (156 mg, 0.42 mmol), and sodium cyanide (41 mg, 0.84 mmol) in DMF:H2O (3:1, 16 mL) was stirred at rt for 18 h. Water (50 mL) was added to the reaction mixture and it was extracted with EtOAc (3×). The organics were combined, washed with brine (2×), dried over Na2SO4, and evaporated to dryness to give an orange oil. The crude oil was purified by flash chromatography eluting with a gradient of EtOAc:hexane (0 to 30 min: 0 to 20% EtOAc) to afford the desired [4-(1,3-benzoxazol-2-yl)-2-bromophenyl]acetonitrile as a yellow solid (M.p. 190–191° C.). 1H NMR (CDCl3, 300 MHz) δ 8.50 (s, 1H), 8.22 (dd, 1H), 7.78 (m, 1H), 7.70 (d, 1H), 7.60 (m, 1H), 7.39 (m, 2H), 3.91 (s, 2H). MS (ESI) 313 (M)+.

Source