Hydrochloric Acid → 1-(1-Benzothiophen-2-yl)cyclobutane-1-carbonitrile

HRID 635369Notes

Reaction equation

HRID 635369 reaction equation
[S:1]1[C:5]([CH2:6][C:7]#[N:8])=[CH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.Br[CH2:14][CH2:15][CH2:16]Br.[OH-].[K+].Cl>CCOCC.CS(C)=O>[S:1]1[C:5]([C:6]2([C:7]#[N:8])[CH2:16][CH2:15][CH2:14]2)=[CH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 80011,3-DibromopropaneHCID 14797Potassium HydroxideHCID 126319232-(1-Benzothiophen-2-yl)acetonitrile

Product 1

HCID 212585231-(1-Benzothiophen-2-yl)cyclobutane-1-carbonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of benzo[b]thiophen-2-acetonitrile (8.05 g) and 1,3-dibromopropane (5.2 ml) in ether (50 ml) was added dropwise under nitrogen over 1 hour to a stirred, ice-cold suspension of finely-powdered potassium hydroxide (13.53 g) in dimethyl sulphoxide (100 ml). When the addition was complete, the mixture was stirred at ambient temperature for 4 hours, then it was added to ice-cold water (200 ml). The resulting mixture was acidified to pH4 by the addition of concentrated hydrochloric acid, then the product was extracted into ether (3×200 ml). The combined extracts were washed with water (500 ml), dried (MgSO4), and the solvent was removed in vacuo to give 1-(benzo[b]thiophen-2-yl)cyclobutanecarbonitrile as a red oil (8.16 g) which was used without purification.

Workup

  1. additionWhen the addition
  2. extractionthe product was extracted into ether (3×200 ml)
  3. washThe combined extracts were washed with water (500 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-cc74a6350d2c491ea96f327a2ebaf8cf
Source dataset
uspto-grants-2001_02
Patent number
US06187802B1

Reaction notes

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