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

HRID 2220303Notes

Reaction equation

HRID 2220303 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-d2f28074afb84230a5da1b3cb61bad21
Source dataset
uspto-grants-2008_08
Patent number
US07417064B2

Reaction notes

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