Hydrogen Bromide → 2-Bromo-1-(6-bromonaphthalen-2-yl)ethanone

HRID 417533Notes

Reaction equation

HRID 417533 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12](=[O:16])[CH:13]=[N+]=[N-])[CH:6]=[CH:5]2.[BrH:17].C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[Br:17][CH2:13][C:12]([C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=2)[CH:8]=1)=[O:16]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 768188121-(6-Bromonaphthalen-2-yl)-2-diazoethanone

Product 1

HCID 126988982-Bromo-1-(6-bromonaphthalen-2-yl)ethanone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-(6-Bromonaphthalen-2-yl)-2-diazoethanone (34.7 g) were dissolved in ethyl acetate (500 mL), and hydrobromic acid solution (21.1 mL, 5.7 M in acetic acid) was added at 0° C. Reaction mixture was stirred 3 hours, NaHCO3 solution (200 mL) was added, and mixture was stirred 10 minutes. Ethyl acetate solution was extracted twice with NaHCO3 solution (50 mL), once with brine (50 mL), and evaporated under vacuum, giving 2-bromo-1-(6-bromonaphthalen-2-yl)-ethanone (33.0 g, crude) as a tan solid.

Workup

  1. customReaction mixture
  2. stirringmixture was stirred 10 minutes
  3. extractionEthyl acetate solution was extracted twice with NaHCO3 solution (50 mL), once with brine (50 mL)
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-c9cf6586a30e4e56a15cf5641be8ecf9
Source dataset
uspto-grants-2012_01
Patent number
US08088368B2

Reaction notes

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