Triethyl phosphite → 1-Fluoro-4-methoxycarbazole

HRID 1824319Notes

Reaction equation

HRID 1824319 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[O:17][CH3:18])([O-])=O.P(OCC)(OCC)OCC>>[F:16][C:14]1[C:15]2[NH:1][C:4]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:10]=2[C:11]([O:17][CH3:18])=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 221477232-(2-Nitrophenyl)-4-fluoroanisole

Product 1

HCID 221477961-Fluoro-4-methoxycarbazoleYield 57%

Procedure

A mixture of 2-(2-nitrophenyl)-4-fluoroanisole (427 mg, 1.73 mmol) and triethyl phosphite (3 mL) was heated to reflux for 3.5 hours. The reaction was cooled and concentrated in vacuo. The crude product was purified via flash silica gel chromatography eluting with 2% ethyl acetate/hexanes followed by 5% ethyl acetate hexanes to give 212 mg of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3.5 hours
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified via flash silica gel chromatography
  6. washeluting with 2% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-7b9b822ae4b64c88a49f02b52a4c43fa
Source dataset
uspto-grants-2006_05
Patent number
US07041684B2

Reaction notes

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