Phosphorus oxychloride → 4-Fluoro-7-methoxy-1-benzothiophene-2-carbonitrile

HRID 2220317Notes

Reaction equation

HRID 2220317 reaction equation
[F:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]([NH2:13])=O)[S:10][C:6]=2[C:5]([O:14][CH3:15])=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>>[F:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]#[N:13])[S:10][C:6]=2[C:5]([O:14][CH3:15])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 23568951HCID 23568951, compound

Product 1

HCID 235689504-Fluoro-7-methoxy-1-benzothiophene-2-carbonitrile

Procedure

A solution of 4-fluoro-7-methoxy-1-benzothiophene-2-carboxamide (0.756 g, 3.3 mmol) in phosphorus oxychloride (6.2 mL, 6.6 mmol) was refluxed for 3 h then cooled and the solvent evaporated in vacuo to give the title compound. Purified by flash chromatography with a gradient of 0-30% ethyl acetate in iso-hexane to give a colourless solid (0.635 g, 91%); δH (300 MHz, CDCl3) 7.95 (1H, s, 3-ArH), 7.10-7.01 (1H, m, ArH), 6.85-6.77 (1H, m, ArH) and 3.98 (3H, s, OCH3).

Workup

  1. temperaturethen cooled
  2. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-a6a558a6946746f7b5a35112f34e4987
Source dataset
uspto-grants-2008_08
Patent number
US07417064B2

Reaction notes

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