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

HRID 923685Notes

Reaction equation

HRID 923685 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-])=O.[CH:12]([Mg]Br)=[CH2:13].[NH4+].[Cl-]>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]2[C:3]=1[NH:9][CH:13]=[CH:12]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 27949042-Bromo-5-chloronitrobenzeneHCID 178418507HCID 178418507, compound

Product 1

HCID 187528737-bromo-4-chloro-1H-indoleYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-bromo-4-chloro-2-nitrobenzene (932 mg, 3.95 mmol) in tetrahydrofuran (10 mL), vinylmagnesium bromide (0.7 M in tetrahydrofuran) (12 mmol) in tetrahydrofuran (15 mL) was added drop wise at −40° C. After 1 h the reaction mixture was poured into saturated NH4Cl. The resulting organic layer was concentrated. The resulting residue was purified using a Teledyne ISCO chromatography system with a gradient eluent system of 2% ethyl acetate in hexane to yield the title compound (400 mg, 44%): 1H NMR (300 MHz, CDCl3) δ 6.73 (t, J=2.8 Hz, 1H), 7.02 (d, J=8.1 Hz, 1H), 7.19-7.39 (m, 2H), 8.43 (s, 1H).

Workup

  1. concentrationThe resulting organic layer was concentrated
  2. customThe resulting residue was purified

Sources & evidence

ORD record
ord-4a945a057d4c4518a86da176e3634d8a
Source dataset
uspto-grants-2016_03
Patent number
US09278985B2

Reaction notes

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