Hydrochloric Acid → HCID 86695336, compound

HRID 403611Notes

Reaction equation

HRID 403611 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10]N)[CH:5]=[C:6]([Br:9])[C:7]=1[Br:8].[CH3:12][CH:13]([CH3:17])[C:14](=O)[CH3:15].Cl.C(=O)([O-])[O-].[Na+].[Na+]>>[Br:1][C:2]1[C:7]([Br:8])=[C:6]([Br:9])[CH:5]=[C:4]2[C:3]=1[C:13]([CH3:17])([CH3:12])[C:14]([CH3:15])=[N:10]2

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 112513-Methyl-2-butanoneHCID 85576207HCID 85576207, compound

Product 1

HCID 86695336HCID 86695336, compoundYield 56.4%

Procedure

1.73 g of 3,4,5-tribromophenylhydrazine and 2 mL (18.5 mmol) of 3-methyl-2-butanone were refluxed for an hour. Next, 15 mL of concentrated HCl were added and refluxed for another 3.5 h. The reaction mixture was neutralized with concentrated aqueous solution of sodium carbonate, and the product was extracted with benzene. The organic layer was dried with MgSO4 and benzene was removed under reduced pressure by a rotary evaporator to yield 1.12 g of 4,5,6-tribromo-2,3,3-trimethyl-3H-indole. 1H-NMR (200 MHz, DMSO-d6), δ, ppm: 7.16 (1H, s, arom.), 2.22 (3H, s, CH3), 1.35 (6H, s, C(CH3)2).

Workup

  1. temperaturerefluxed for another 3.5 h
  2. extractionthe product was extracted with benzene
  3. dry with materialThe organic layer was dried with MgSO4 and benzene
  4. customwas removed under reduced pressure by a rotary evaporator

Sources & evidence

ORD record
ord-36a87dfc4a0243d1ac25f3051591d3b1
Source dataset
uspto-grants-2014_06
Patent number
US08748446B2

Reaction notes

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