hydroxylamine-O-sulfonic acid → 3-Bromo-5-methylthiophene-2-carbonitrile

HRID 2054543Notes

Reaction equation

HRID 2054543 reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([CH3:7])[S:4][C:3]=1[CH:8]=O.[NH2:10]OS(O)(=O)=O>O>[Br:1][C:2]1[CH:6]=[C:5]([CH3:7])[S:4][C:3]=1[C:8]#[N:10]

Participants

4

Reactant 2

HCID 76284hydroxylamine-O-sulfonic acidHCID 8188853-Bromo-5-methylthiophene-2-carbaldehyde

Product 1

HCID 691079883-Bromo-5-methylthiophene-2-carbonitrileYield 83.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 3-bromo-5-methyl-2-thiophenecarboxaldehyde (500 mg) in water (10 ml) was added hydroxylamine-O-sulfonic acid (330 mg). The mixture was heated to 50° C. for 12 h and allowed to cool. The mixture was then extracted with ethyl acetate (3×50 ml). The combined organic layers were washed (brine), dried (MgSO4), filtered and evaporated to leave the sub-title compound (410 mg) as a brown solid.

Workup

  1. temperatureto cool
  2. extractionThe mixture was then extracted with ethyl acetate (3×50 ml)
  3. washThe combined organic layers were washed (brine)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-203885634b22458bb48375919679ef63
Source dataset
uspto-grants-2008_02
Patent number
US07329686B2

Reaction notes

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