Water → 2-(5-bromothiophen-2-yl)acetonitrile

HRID 1484905Notes

Reaction equation

HRID 1484905 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]#[N:8].C1C(=O)N([Br:16])C(=O)C1.O>CN(C=O)C>[Br:16][C:5]1[S:1][C:2]([CH2:6][C:7]#[N:8])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 728802-Thienylacetonitrile

Product 1

HCID 8188762-(5-bromothiophen-2-yl)acetonitrileYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(thiophen-2-yl)acetonitrile (1.23 g, 10 mmol, 1.0 eq) in DMF (10 mL), NBS (1.96 g, 11 mmol, 1.1 eq) was added. The mixture was stirred at room temperature for 2 h. Water was added to the reaction mixture. After extraction with EtOAc (3×), the organic layers were washed with water, brine, dried (Na2SO4) and filtered. The filtrate was concentrated and the resulting residue was purified by silica gel chromatography (petroleum/EtOAc from 100:1 to 10:1) to affords 2-(5-bromothiophen-2-yl)acetonitrile (738 mg, 60%). LC-MS (m/z)=202 [M+H]+

Workup

  1. extractionAfter extraction with EtOAc (3×)
  2. washthe organic layers were washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe resulting residue was purified by silica gel chromatography (petroleum/EtOAc from 100:1 to 10:1)

Sources & evidence

ORD record
ord-fb32b1ca83e34f699f5b0018f719393f
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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