Trimethylsilyl cyanide → [4-(1,3-Benzoxazol-2-yl)-2-(trifluoromethyl)phenyl]acetonitrile

HRID 7694

Reaction equation

HRID 7694 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][C:4]=1[C:18]([F:21])([F:20])[F:19].[C:22]([Si](C)(C)C)#[N:23].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C(#N)C>[O:10]1[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=[C:9]1[C:6]1[CH:7]=[CH:8][C:3]([CH2:2][C:22]#[N:23])=[C:4]([C:18]([F:21])([F:20])[F:19])[CH:5]=1

Participants

5

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 2724141Tetrabutylammonium FluorideHCID 219909772-[4-(Bromomethyl)-3-(trifluoromethyl)phenyl]-1,3-benzoxazole

Product 1

HCID 10125560[4-(1,3-Benzoxazol-2-yl)-2-(trifluoromethyl)phenyl]acetonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 2-[4-(bromomethyl)-3-(trifluoromethyl)phenyl]-1,3-benzoxazole (528 mg, 1.5 mmol) and cyanotrimethylsilane (0.30 mL, 2.2 mmol) in acetonitrile (19 mL) was added TBAF (1.0M in THF, 2.2 mL, 2.2 mmol) and the mixture was stirred at rt for 2 h. The solvent was removed in vacuo and the crude was purified by flash chromatography eluting with EtOAc:hexanes (1:9) to afford the desired [4-(1,3-benzoxazol-2-yl)-2-(trifluoromethyl)phenyl]acetonitrile as a colorless solid. 1H NMR (CDCl3, 300 MHz) δ 8.60 (s, 1H), 8.48 (d, 1H), 7.88 (d, 1H), 7.82 (m, 1H), 7.63 (m, 1H), 7.43 (m, 2H), 4.05 (s, 2H). MS (ESI) 303 (M+H)+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude was purified by flash chromatography
  3. washeluting with EtOAc:hexanes (1:9)

Sources & evidence

ORD record
ord-26845d3d550d49b5a8a35ee75d6d3a4d
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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