1-Bromo-2-nitrobenzene → 7-Bromoindole

HRID 1173094Notes

Reaction equation

HRID 1173094 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[Br:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-])=O.[Cl-].[NH4+]>O1CCCC1>[Br:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:7]=1[NH:12][CH:2]=[CH:1]2

Participants

5

Reactant 3

HCID 113411-Bromo-2-nitrobenzeneHCID 25517Ammonium ChlorideHCID 178418507HCID 178418507, compound

Product 1

HCID 27570207-Bromoindole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

100 ml (100 mmol) of a tetrahydrofuran solution containing 1.0 M vinylmagnesium bromide was added to a tetrahydrofuran solution (250 ml) containing 5.05 g (25 mmol) of 2-bromonitrobenzene at −40° C. in nitrogen atmosphere, followed by stirring as it was for 40 minutes. The reaction mixture was poured into 500 ml of an aqueous saturated ammonium chloride, and the mixture was extracted with ethyl ether. The extract was dried over magnesium sulfate and concentrated. Then, the residue was purified by silica gel column chromatography, to give 2.89 g of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl ether
  2. dry with materialThe extract was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThen, the residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d2621e0b288a4adc95637f5267812e34
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

Loading…