1-[(4-Chlorophenyl)sulfanyl]propan-2-one → 19404-18-3

HRID 1603726Notes

Reaction equation

HRID 1603726 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10](=O)[CH3:11])=[CH:4][CH:3]=1>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[S:8][CH:9]=[C:10]([CH3:11])[C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 3217461-[(4-Chlorophenyl)sulfanyl]propan-2-one

Product 1

HCID 31731719404-18-3Yield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

1-[(4-Chlorophenyl)thio}-2-propanone (50 g, 0.25 mol) was added to polyphosphoric acid (300 g) and the mixture was stirred as the temperature was gradually raised to 120° C.. as an exotherm started. The mixture was stirred at 130° C.. for 1 hour, diluted with water, extracted with ethyl ether and the organic phase was dried and concentrated. The residue was stirred in methanol (200 ml), filtered and the filtrate concentrated to give 17.5 g (40%) of 5-chloro-3-methylbenzo(b)thiophene: bp 120° C.. (0.6 mm Hg).

Workup

  1. stirringThe mixture was stirred at 130° C.
  2. extractionextracted with ethyl ether
  3. customthe organic phase was dried
  4. concentrationconcentrated
  5. stirringThe residue was stirred in methanol (200 ml)
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-81125d4f78374715b91ba61cda306ae3
Source dataset
uspto-grants-1999_11
Patent number
US05990128

Reaction notes

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