Sodium Cyanide → 2-(1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)acetonitrile

HRID 1673001Notes

Reaction equation

Br[CH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[N:6]=[C:5]([C:15]([F:18])([F:17])[F:16])[CH:4]=1.[C-:19]#[N:20].[Na+]>CN(C=O)C.CCOCC.O>[Cl:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[N:7]1[C:3]([CH2:2][C:19]#[N:20])=[CH:4][C:5]([C:15]([F:18])([F:17])[F:16])=[N:6]1

Participants

Conditions

Temperature: 50 °C

Procedure

Into a 250 mL flask was weighed 11.3 g of 5-(bromomethyl)-1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazole (33 mmol) which was then dissolved in 40 mL of dry DMF. The resulting solution was treated with 2.5 g of sodium cyanide (52 mmol). The resulting suspension was heated to 50° C. After 4 hours at 50° C., heating was discontinued and the reaction was allowed to cool to room temperature. After standing at room temperature for 2 days the reaction was diluted with ether and H2O. The layers were separated and the aqueous layer was extracted with ether (4×). The combined organic layers were washed with H2O (3×), then brine (2×), dried (Na2SO4), filtered and concentrated in vacuo to afford crude 2-(1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)acetonitrile as a red oil, yield 8.2 g (86%), 1H NMR (400 MHz, CDCl3): δ 7.62-7.46 (m, 4H), 6.82 (s, 1H), 3.9-3.4 (broad hump, 2H).

Workup

customInto a 250 mL flask was weighed
temperatureheating
temperatureto cool to room temperature
waitAfter standing at room temperature for 2 days
customThe layers were separated
extractionthe aqueous layer was extracted with ether (4×)
washThe combined organic layers were washed with H2O (3×)
dry with materialbrine (2×), dried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-610f8d777f09446d993bbfb80ec14b6e
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998995B2

Reaction notes

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