Dimethylformamide → 5-Bromo-4-methylthiophene-2-carbaldehyde

HRID 2076700Notes

Reaction equation

HRID 2076700 reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[Br:11][C:12]1[S:13][CH:14]=[CH:15][C:16]=1[CH3:17].[OH-].[Na+]>>[Br:11][C:12]1[S:13][C:14]([CH:8]=[O:9])=[CH:15][C:16]=1[CH3:17]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 843142-Bromo-3-methylthiophene

Product 1

HCID 164141925-Bromo-4-methylthiophene-2-carbaldehydeYield 6,250.6%

Procedure

Phosphoryl chloride (5.3 ml, 0.57 mmol) was added dropwise to N,N-dimethylformamide (8.8 ml, 0.11 mmol) under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. 2-Bromo-3-methylthiophene (5.00 g, 28.2 mmol) was added dropwise thereto under ice-cooling and the mixture was stirred at 50° C. for 6 hours. The reaction mixture was neutralized with a 2N aqueous sodium hydroxide solution under ice-cooling. The reaction mixture was extracted with diethyl ether and the organic layer was dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=5/1) to give 5-bromo-4-methyl-2-thiophenecarbaldehyde (1.41 g, yield: 24%).

Workup

  1. temperaturecooling
  2. temperatureunder ice-cooling
  3. stirringthe mixture was stirred at 50° C. for 6 hours
  4. temperaturecooling
  5. extractionThe reaction mixture was extracted with diethyl ether
  6. dry with materialthe organic layer was dried with anhydrous sodium sulfate
  7. customThe residue obtained
  8. customby removing the solvent under reduced pressure
  9. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-721e909c9e7b47e49e8f483f5d52274f
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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