Hydrochloric Acid → HCID 86695336, compound

HRID 1854646Notes

Reaction equation

HRID 1854646 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-b1ab6a32dfcc4c4fb1ef80ab9732b6f3
Source dataset
uspto-grants-2015_02
Patent number
US08962797B2

Reaction notes

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