Ammonium Chloride → 7-Fluoro-1H-indole

HRID 583062

Reaction equation

HRID 583062 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 Fluoronitrobenzene (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 one hour. Poured onto saturated ammonium chloride (600 ml). Separated and aqueous extracted with diethyl ether (2×200 ml). 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.

Workup

  1. customSeparated
  2. extractionaqueous extracted with diethyl ether (2×200 ml)
  3. dry with materialDried (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-cab904f2e9934dfcbe038bb6b012a84e
Source dataset
uspto-grants-1999_07
Patent number
US05929072

Linked notes

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