Water → 3-(5-Bromo-2-methyl-thiophen-3-yl)-propionitrile

HRID 1268851Notes

Reaction equation

HRID 1268851 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH2:7][CH2:8][C:9]#[N:10].[Br:11]Br.O>C(O)(=O)C>[Br:11][C:4]1[S:3][C:2]([CH3:1])=[C:6]([CH2:7][CH2:8][C:9]#[N:10])[CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 184465313-(2-Methylthiophen-3-yl)-propionitrile

Product 1

HCID 184465373-(5-Bromo-2-methyl-thiophen-3-yl)-propionitrileYield 68.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-(2-methylthiophen-3-yl)-propionitrile 60 (320 mg, 2.1 mmol) in acetic acid (5 mL) was treated with bromine (0.12 mL, 2.3 mmol) and the mixture stirred at rt for 1 hour. Water was added and the mixture was extracted with EtOAc (2×20 mL). The combined organics were washed with water and dried over MgSO4. Removal of the solvent followed with silica gel column chromatography (eluent: DCM/hexane, 1/1) gave 61 as a colorless liquid (330 mg). 1H NMR (400 MHz, CDCl3) δ: 2.35 (s, 3H), 2.53 (t, J=10.5 Hz, 2H), 2.84 (t, J=10.5 Hz, 2H) 6.80 (s, 1H).

Workup

  1. extractionthe mixture was extracted with EtOAc (2×20 mL)
  2. washThe combined organics were washed with water
  3. dry with materialdried over MgSO4
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-6027bdf7873348a1a8ce13d2a6c7332c
Source dataset
uspto-grants-2007_04
Patent number
US07199119B2

Reaction notes

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