Water → [4-(1,3-Benzoxazol-2-yl)-2-chlorophenyl]acetonitrile

HRID 7718

Reaction equation

HRID 7718 reaction equation
[C-]#N.[Na+].Br[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)=[CH:8][C:7]=1[Cl:21].[CH3:22][N:23](C=O)C.O>[Cl-].[Na+].O>[O:13]1[C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=[C:12]1[C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C:22]#[N:23])=[C:7]([Cl:21])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 219909852-[4-(Bromomethyl)-3-chlorophenyl]-1,3-benzoxazole

Product 1

HCID 10286072[4-(1,3-Benzoxazol-2-yl)-2-chlorophenyl]acetonitrile

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A slurry of NaCN (435 mg, 8.9 mmol), 2-[4-(bromomethyl)-3-chlorophenyl]-1,3-benzoxazole (940 mg, 2.9 mmol), DMF (30 mL) and H2O (30 mL) was stirred at rt for 12 h. The reaction mixture was poured into brine (250 mL) and filtered. The resultant colorless solid was purified by flash chromatography on silica gel (EtOAc:hexanes 1:9) to afford the desired [4-(1,3-benzoxazol-2-yl)-2-chlorophenyl]acetonitrile as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 8.32 (s, 1H), 8.19 (dd, 1H), 7.77–7.80 (m, 1H), 7.70 (d, 1H), 7.59–7.61 (m, 1H), 7.38–7.41 (m, 2H), 3.92 (s, 2H). MS (ESI) 269 (M+H)+.

Workup

  1. filtrationfiltered
  2. customwas purified by flash chromatography on silica gel (EtOAc:hexanes 1:9)

Sources & evidence

ORD record
ord-6548a23538894aa79436e59d15d367bc
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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