Hydrochloric Acid → 7-fluoro-4-methoxy-1-benzothiophen-2(3H)-one

HRID 1822957Notes

Reaction equation

HRID 1822957 reaction equation
[F:1][C:2]1[C:10]2[S:9][C:8](N(C)C)=[CH:7][C:6]=2[C:5]([O:14][CH3:15])=[CH:4][CH:3]=1.Cl.C1C[O:20]CC1>>[F:1][C:2]1[C:10]2[S:9][C:8](=[O:20])[CH2:7][C:6]=2[C:5]([O:14][CH3:15])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 22171134N-(7-fluoro-4-methoxy-1-benzothien-2-yl)-N,N-dimethylamine

Product 1

HCID 235689637-fluoro-4-methoxy-1-benzothiophen-2(3H)-oneYield 84%

Conditions

Temperature
80 °C

Procedure

To a solution of N-(7-fluoro-4-methoxy-1-benzothien-2-yl)-N,N-dimethylamine (1.73 g, 7.7 mmol) in THF (25 mL) was added aqueous hydrochloric acid (1 N, 25 mL) and this was heated to 80° C. for 3 h. After cooling to room temperature then extracted with ether (100 mL), dried (MgSO4) and the solvent evaporated in vacuo to give a yellow solid. The residue was purified by flash chromatography in 5% ethyl acetate in hexane to give (1.3 g, 84%) of the title compound; δH (300 MHz, CHCl3) 6.97–6.87 (1H, m, ArH), 6.62–6.55 (1H, m, ArH), 3.91 (2H, s, CH2) and 3.85 (3H, s, OCH3).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthen extracted with ether (100 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvent evaporated in vacuo
  5. customto give a yellow solid
  6. customThe residue was purified by flash chromatography in 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-95c9deb7ce7b4583bad325432a92dac9
Source dataset
uspto-grants-2006_05
Patent number
US07037932B2

Reaction notes

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