Ammonium Chloride → 4-Bromo-7-chloro-1H-indole

HRID 2278392Notes

Reaction equation

HRID 2278392 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([N+:9]([O-])=O)[CH:3]=1.[CH:12]([Mg]Br)=[CH2:13].[NH4+].[Cl-]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]2[C:3]=1[CH:12]=[CH:13][NH:9]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 8179745-Bromo-2-chloronitrobenzeneHCID 178418507HCID 178418507, compound

Product 1

HCID 533991604-Bromo-7-chloro-1H-indoleYield 44.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4-bromo-1-chloro-2-nitro-benzene (14 g, 0.059 mol) in 400 mL THF at −40° C. was added dropwise vinylmagnesium bromide (177 mL of 1.0M solution in THF, 0.177 mol). The reaction mixture was stirred for 2 hrs at 40° C. Aqueous NH4Cl was added and the mixture extracted with ether. The organic phase was dried over Na2SO4, concentrated and the residue purified by silica gel column chromatography to give the title compound (6 g, 44%).

Workup

  1. extractionthe mixture extracted with ether
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customthe residue purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5cee3af14d754d7789e947f23e1202c4
Source dataset
uspto-grants-2015_09
Patent number
US09133180B2

Reaction notes

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