Hydrogen Bromide → 1-Bromo-4-(bromoacetyl)naphthalene

HRID 417525Notes

Reaction equation

HRID 417525 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12](=[O:16])[CH:13]=[N+]=[N-])=[CH:4][CH:3]=1.[BrH:17].C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[Br:17][CH2:13][C:12]([C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([Br:1])=[CH:3][CH:4]=1)=[O:16]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 723379011-(4-Bromonaphthalen-1-yl)-2-diazoethanone

Product 1

HCID 596110431-Bromo-4-(bromoacetyl)naphthaleneYield 51%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-(4-Bromonaphthalen-1-yl)-2-diazoethanone (13.8 g) was dissolved in ethyl acetate (200 mL), and hydrobromic acid solution (8.4 mL, 5.7 M in acetic acid) was added at 0° C. Reaction mixture was stirred 15 minutes, NaHCO3 solution (100 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. The oil was dissolved in DCM and purified by chromatography (0-20% ethyl acetate:hexane), giving 2-bromo-1-(4-bromo-naphthalen-1-yl)-ethanone (6.67 g, 51%) 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
  5. dissolutionThe oil was dissolved in DCM
  6. custompurified by chromatography (0-20% ethyl acetate:hexane)

Sources & evidence

ORD record
ord-c992491776d343e99f613d424e0794d6
Source dataset
uspto-grants-2012_01
Patent number
US08088368B2

Reaction notes

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