Sodium Cyanide → 4-(Trifluoromethoxy)phenylacetonitrile

HRID 1843964Notes

Reaction equation

HRID 1843964 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]([F:13])([F:12])[F:11])=[CH:5][CH:4]=1.[C-:14]#[N:15].[Na+]>CS(C)=O>[F:11][C:10]([F:13])([F:12])[O:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][C:14]#[N:15])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 1427851-(Bromomethyl)-4-(trifluoromethoxy)benzene

Product 1

HCID 1426764-(Trifluoromethoxy)phenylacetonitrileYield 96.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

Using analogous conditions and workup as described for the preparation of I-24a above, 1-(bromomethyl)-4-(trifluoromethoxy)benzene (5 g, 19.607 mmol) in DMSO (30 mL) was reacted with NaCN (1.44 g, 35.1864 mmol). The resulting mixture was stirred at 90° C. for 1 hour to afford 3.8 g of the product (95% yield). 1H NMR (300 MHz, CDCl3): 7.45-7.20 (m, 4H), 3.8 (s, 2H)

Sources & evidence

ORD record
ord-34ee7b97cef74737ac0704b4a1474116
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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