Triethyl phosphite → 1-Fluoro-4-methoxycarbazole

HRID 2119832Notes

Reaction equation

HRID 2119832 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. Yield: 57%. MS(FD).

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-718d788756954cb28bae4b741220f75c
Source dataset
uspto-grants-2004_02
Patent number
US06686372B2

Reaction notes

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