Bromine → HCID 86631600, compound

HRID 2194688Notes

Reaction equation

HRID 2194688 reaction equation
[F:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([CH:13]=[O:14])[S:11][CH:12]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:15]Br>C(O)(=O)C.CN(C)C=O>[Br:15][C:12]1[S:11][C:10]([CH:13]=[O:14])=[CH:9][C:8]=1[C:7]1[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 86631590HCID 86631590, compound

Product 1

HCID 86631600HCID 86631600, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

4-(2-Fluoropyridin-3-yl)thiophene-2-carbaldehyde (3.35 g) was dissolved in acetic acid (20 mL) and N,N-dimethylformamide (20 mL), and bromine (7.77 g) was added at room temperature. The reaction mixture was stirred overnight and concentrated under reduced pressure. The residue was weakly basified with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium thiosulfate solution, saturated aqueous sodium hydrogen carbonate solution and saturated brine in this order, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane:ethyl acetate=6:1→3:1), and the obtained solid was washed with diisopropyl ether to give the title compound as a pale-yellow powder (yield 1.79 g, 39%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium thiosulfate solution, saturated aqueous sodium hydrogen carbonate solution and saturated brine in this order
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane:ethyl acetate=6:1→3:1)
  7. washthe obtained solid was washed with diisopropyl ether

Sources & evidence

ORD record
ord-5cb35b11dd044ec3a6ac35cdcf98d49a
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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