Sodium Carbonate → 5-(3-bromophenyl)thiophene-2-carbaldehyde

HRID 486830Notes

Reaction equation

HRID 486830 reaction equation
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[CH:8]=[C:9]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[CH:10]=[CH:11][CH:12]=1.[C:18](=O)([O-])[O-:19].[Na+].[Na+]>CN(C)C=O>[CH:18]([C:15]1[S:14][C:13]([C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([Br:6])[CH:8]=2)=[CH:17][CH:16]=1)=[O:19]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 12060894HCID 12060894, compound

Product 1

HCID 35780555-(3-bromophenyl)thiophene-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phosphorus oxychloride (1.15 mL; 15.4 mM) was added slowly to stirring dimethylformamide (0.95 mL; 12.2 mM) at -10° under nitrogen. The resulting mixture was stirred for 15 mins. 2-(3'-bromophenyl)thiophene (2.12 g; 9 mM) was then added. The reaction mixture was then warmed slowly to 110° over a period of 1 hr. cooled and poured into ice, and cautiously neutralized with sodium carbonate. Extraction with ethyl acetate and drying the organic phase with anhydrous magnesium sulfate provided upon concentration 2.16 g of the desired aldehyde as an oily solid.

Workup

  1. temperatureThe reaction mixture was then warmed slowly to 110° over a period of 1 hr
  2. temperaturecooled
  3. additionpoured into ice
  4. extractionExtraction with ethyl acetate
  5. dry with materialdrying the organic phase with anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-f9720aee493041d4850b1311a1b1bd64
Source dataset
uspto-grants-1994_03
Patent number
US05292879

Reaction notes

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