N-bromobutanimide → 4-(3-Cyano-2-thienyl)benzyl bromide

HRID 1769203Notes

Reaction equation

HRID 1769203 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[CH:11][C:12]=2[C:13]#[N:14])=[CH:4][CH:3]=1.[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N1(C2CCCCCCCC2)CCCCCCCC1>[Br:15][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][CH:10]=[CH:11][C:12]=2[C:13]#[N:14])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 200928362-(4-Methylphenyl)thiophene-3-carbonitrile

Product 1

HCID 200928574-(3-Cyano-2-thienyl)benzyl bromideYield 67.1%

Reagents, catalysts & solvents 2

HCID 18706763HCID 18706763, compoundCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-(4-methylphenyl)-3-cyanothiophene (1.5 g, 7.5 mmol), N-bromosuccinimide (1.34 g, 7.5 mmol), and azabicyclononane (20 mg) in carbon tetrachloride was irradiated with UV light for one hour. The reaction mixture was cooled, and the solid filtered off. The filtrate was concentrated, and the residue purified by flash chromatography, eluting with 5% ethyl acetate/hexane, to yield 2-(4-bromomethylphenyl)-3-cyanothiophene 1.4 g, m.p. 68-75 (slightly impure, used as such).

Workup

  1. customwas irradiated with UV light for one hour
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe solid filtered off
  4. concentrationThe filtrate was concentrated
  5. customthe residue purified by flash chromatography
  6. washeluting with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-70b25ef575a847cf88367ef29622c2c9
Source dataset
uspto-grants-1995_01
Patent number
US05380739

Reaction notes

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