Ethanol → 4-(Trifluoromethoxy)phenylacetonitrile

HRID 2306163Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

150 g of ethanol, 28 ml of water, and 31.5 g of sodium cyanide were initially charged, and 127.5 g of 4-bromomethyl-1-trifluoromethoxybenzene were added. The reaction mixture was stirred at 90° C. for 3.5 hours and then poured into 250 ml of water and extracted twice with 50 ml portions of dichloromethane. The combined organic phases were concentrated and the residue was distilled at 18 hPa. This gave 81.5 g of (4-trifluoromethoxyphenyl)acetonitrile as a colorless liquid (76.3% of theory) of b.p. 110-112° C.

Workup

extractionextracted twice with 50 ml portions of dichloromethane
concentrationThe combined organic phases were concentrated
distillationthe residue was distilled at 18 hPa

Sources & evidence

ORD record: ord-5494aa1c9e6b4b0aa5c24cff33af63cf
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06441239B1

Reaction notes

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