Acetic Acid → 4-Bromo-3-methyl-2-thiophenecarbonitrile

HRID 1386122Notes

Reaction equation

HRID 1386122 reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([C:8]#[N:9])[S:5][C:6]=1Br.C(O)(=O)C>[Zn].O>[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([C:8]#[N:9])[S:5][CH:6]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 21717669HCID 21717669, compound

Product 1

HCID 217176714-Bromo-3-methyl-2-thiophenecarbonitrileYield 96.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Conditions

Temperature
102.5 °C

Procedure

A mixture of 0.400 g (1.42 mmol) of 4,5-dibromo-3-methyl-2-thiophenecarbonitrile, 0.186 g (2.85 mmol) of zinc dust, 4 mL of acetic acid and 1 mL of water was heated at 100-105° C. for 45 minutes. After cooling, the solvents were removed under reduced pressure and the residue was dissolved in 10 mL of ether and washed with water (2×5 mL) and dilute, aqueous sodium carbonate solution (1×5 mL). After drying (sodium sulfate), the ether was removed on the rotovap to afford 0.276 g (96%) of an off-white solid: mp 54-58° C.; 1H NMR (CDCl3) 7.47 (s, 1H, ring-H) and 2.42 (s, 3H, CH3); GC-MS (EI) 201/203 (M+).

Workup

  1. temperatureAfter cooling
  2. customthe solvents were removed under reduced pressure
  3. dissolutionthe residue was dissolved in 10 mL of ether
  4. washwashed with water (2×5 mL)
  5. additiondilute
  6. dry with materialAfter drying (sodium sulfate)
  7. customthe ether was removed on the rotovap

Sources & evidence

ORD record
ord-db4d1873a3f748eca7facdb8a7e63b58
Source dataset
uspto-grants-2001_07
Patent number
US06265424B1

Reaction notes

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