HCID 70284941, compound → 1-(5-Chloro-1-benzothiophen-3-yl)ethan-1-one

HRID 362264Notes

Reaction equation

HRID 362264 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[S:6][CH2:7][CH:8]([C:9](=[O:18])[CH2:10]OC3C=CC=CC=3)[C:4]=2[CH:3]=1>S(=O)(=O)(O)O.C(O)(=O)C>[C:9]([C:8]1[C:4]2[CH:3]=[C:2]([Cl:1])[CH:20]=[CH:19][C:5]=2[S:6][CH:7]=1)(=[O:18])[CH3:10]

Participants

4

Reactant 1

HCID 70284941HCID 70284941, compound

Product 1

HCID 113901951-(5-Chloro-1-benzothiophen-3-yl)ethan-1-oneYield 101.2%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 1-(5-chloro-2,3-dihydrobenzo[b]thiophen-3-yl)-2-phenoxyethanone (15.3 g), acetic acid (75 ml) and concentrated sulphuric acid (15 drops) was heated at 90°-95° C. under nitrogen for 20 hours, then the solvent was removed in vacuo. The residue was partitioned between dichloromethane (250 ml) and 5M aqueous sodium hydroxide solution (100 ml), then the aqueous phase was separated and washed with dichloromethane (50 ml). The combined dichloromethane solutions were washed with water (100 ml), dried (MgSO4), and the solvent removed in vacuo to leave 3-acetyl-5-chlorobenzo[b]thiophen as a red-brown oil (10.7 g) which solidified slowly at ambient temperature.

Workup

  1. temperaturewas heated at 90°-95° C. under nitrogen for 20 hours
  2. customthe solvent was removed in vacuo
  3. customThe residue was partitioned between dichloromethane (250 ml) and 5M aqueous sodium hydroxide solution (100 ml)
  4. customthe aqueous phase was separated
  5. washwashed with dichloromethane (50 ml)
  6. washThe combined dichloromethane solutions were washed with water (100 ml)
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-2718b0ddff354de397c9dcea6bf62b24
Source dataset
uspto-grants-1999_02
Patent number
US05869492

Reaction notes

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