Water → 2-Acetyl-4-iodo benzo[b]thiophene

HRID 1394596Notes

Reaction equation

HRID 1394596 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([I:10])[C:3]=1[CH:4]=O.[SH:11][CH2:12][C:13](=[O:15])[CH3:14].CCN(CC)CC.O>CS(C)=O>[C:13]([C:12]1[S:11][C:2]2[CH:9]=[CH:8][CH:7]=[C:6]([I:10])[C:3]=2[CH:4]=1)(=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 5201441-Mercapto-2-propanoneHCID 110969762-Fluoro-6-iodobenzaldehyde

Product 1

HCID 179527062-Acetyl-4-iodo benzo[b]thiopheneYield 61%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2.53 g (10.1 mmol) of 2-fluoro-6-iodo benzaldehyde, 1.0 g (11.1 mmol) of mercapto-2-propanone and 3.5 mL (2.5 g, 25 mmol) of Et3N in 15 mL of DMSO was heated to 80° C. overnight. After cooling to room temperature, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water (2 times), brine and dried over MgSO4. After evaporation of the solvents, the crude product was purified over silica gel column chromatography to afford 1.85 g (6.12 mmol, yield: 61%) of 2-acetyl-4-iodo benzo[b]thiophene as an orange powder. 1H-NMR (CDCl3), δ: 7.97 (s, 1H), 7.83 (d, J=7.9 Hz, 2H), 7.16 (t, J=7.9 Hz, 1H), 2.70 (s, 3H).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water (2 times), brine
  4. dry with materialdried over MgSO4
  5. customAfter evaporation of the solvents
  6. customthe crude product was purified over silica gel column chromatography

Sources & evidence

ORD record
ord-0fb202ca7e9b43deac9b3b50c93c556b
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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