Ammonium Chloride → 4-Bromo-7-(1-methylethyl)-1H-indole

HRID 1945281Notes

Reaction equation

HRID 1945281 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH3:14])[CH3:13])=[C:8]([N+:15]([O-])=O)[CH:7]=1.[NH4+].[Cl-]>C1COCC1>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH3:14])[CH3:13])=[C:8]2[C:7]=1[CH:1]=[CH:2][NH:15]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 57481473HCID 57481473, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 592677634-Bromo-7-(1-methylethyl)-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Vinyl magnesium bromide (1 M in THF) (98 mL, 98 mmol) was added to 4-bromo-1-isopropyl-2-nitrobenzene (4 g, 16.39 mmol) in THF (60 mL) at −40° C. The reaction mixture was stirred for 1 h, then poured into saturated aqueous NH4Cl and extracted with ether. The combined ethereal extracts were dried (MgSO4) and concentrated. Chromatography over silica eluting with 1-20% EtOAc/hexanes afforded the title compound. LC-MS: calculated for C11H12BrN 237,02, observed m/e 238.2 (M+H)+ Rt (1.96/4 min.).

Workup

  1. extractionextracted with ether
  2. dry with materialThe combined ethereal extracts were dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e47b188e059d459e9e7a22282b7bde8e
Source dataset
uspto-grants-2013_03
Patent number
US08394969B2

Reaction notes

Loading…