Ammonium Chloride → 7-fluoro-2-methyl-1H-indole

HRID 18502Notes

Reaction equation

HRID 18502 reaction equation
[C:1]([Mg]Br)([CH3:3])=[CH2:2].[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-])=O.[NH4+].[Cl-]>C1COCC1>[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:8]=1[NH:13][C:1]([CH3:3])=[CH:2]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 738951-Fluoro-2-nitrobenzeneHCID 178456138HCID 178456138, compound

Product 1

HCID 151044237-fluoro-2-methyl-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

1600 ml of a 0.5M solution of isopropenylmagnesium bromide in THF are cooled to −25° C. under an argon atmosphere, a solution of 37.65 g of 2-fluoronitrobenzene in 250 ml of THF is then added dropwise and the mixture is left stirring at −20° C. for 1 hour. The reaction mixture is poured into a saturated NH4Cl solution, the aqueous phase is extracted with ether and the combined organic phases are concentrated under vacuum. The residue is taken up in water and extracted with DCM, the organic phase is washed with water and with a saturated NaCl solution and dried over MgSO4, and the solvent is evaporated under vacuum. The residue is chromatographed on silica gel, elution being carried out with a cyclohexane/EtOAc mixture (95/5; v/v). 12.35 g of the expected compound are obtained.

Workup

  1. waitthe mixture is left
  2. extractionthe aqueous phase is extracted with ether
  3. concentrationthe combined organic phases are concentrated under vacuum
  4. extractionextracted with DCM
  5. washthe organic phase is washed with water and with a saturated NaCl solution
  6. dry with materialdried over MgSO4
  7. customthe solvent is evaporated under vacuum
  8. customThe residue is chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-574c4a03c68d4feba70665e423d45be3
Source dataset
uspto-grants-2010_06
Patent number
US07741363B2

Reaction notes

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