Ethanol → 2-(5-Chloro-2-phenyl-1-benzothiophen-3-yl)acetonitrile

HRID 2164138Notes

Reaction equation

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

Participants

Conditions

Temperature: 52 °C

Procedure

13.0 Parts by weight of 3-bromomethyl-5-chloro-2-phenylbenzo[b]thiophene, 5.1 parts by weight of potassium cyanide and 1.5 parts by weight of potassium iodide are suspended in 250 parts by volume of 95% ethanol and heated at 52° C. under a nitrogen atmosphere for 22.5 hours. The reaction mixture is then diluted with 250 parts by volume of water and stirred for an additional 0.5 hour. The resulting precipitate is separated from the reaction mixture by filtration. Crystallization of this precipitate from ethyl acetate affords as a white crystalline solid 5-chloro-2-phenylbenzo[b]thiophene-3-acetonitrile, melting at 158°-160° C. This compound is represented by the following structural formula. ##STR12##

Workup

customThe resulting precipitate is separated from the reaction mixture by filtration
customCrystallization of this precipitate from ethyl acetate

Sources & evidence

ORD record: ord-7038ea634a134b9aa498281add0a934c
Source dataset: uspto-grants-1979_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04137414

Reaction notes

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