Ammonium Chloride → 7-Fluoro-1H-indole

HRID 2268766Notes

Reaction equation

HRID 2268766 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[CH:11]([Mg]Cl)=[CH2:12].[Cl-].[NH4+]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[NH:8][CH:12]=[CH:11]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 738951-Fluoro-2-nitrobenzeneHCID 178461836HCID 178461836, compound

Product 1

HCID 27745047-Fluoro-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-50 °C

Procedure

2-Fluoro-1-nitrobenzene (20.0 g, 0.142 mol) was dissolved in dry tetrahydrofuran (400 ml) and cooled to −50° C. Vinylmagnesium chloride (288 ml, 15% wt/vol) was added at −45° C. and stirred at this temperature for 1 hr. The reaction mixture was then poured onto saturated ammonium chloride (600 ml), separated and the aqueous layer extracted with diethyl ether (2×200 ml) then dried (MgSO4), filtered and concentrated in vacuo to yield a dark oil which was purified by column chromatography on silica using toluene as mobile phase. Fractions concentrated to yield a crystalline solid. (Tetrahedron Lett. (1989), 30(16), 2129-32)

Workup

  1. customseparated
  2. extractionthe aqueous layer extracted with diethyl ether (2×200 ml)
  3. dry with materialthen dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto yield a dark oil which
  7. customwas purified by column chromatography on silica
  8. concentrationFractions concentrated
  9. customto yield a crystalline solid

Sources & evidence

ORD record
ord-b015316e8bf44e4480ffecea49847fb3
Source dataset
uspto-grants-2001_12
Patent number
US06329366B1

Reaction notes

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