(6-Bromonaphthalen-2-yl)methanol → 6-Bromonaphthalene-2-carbaldehyde

HRID 541496Notes

Reaction equation

HRID 541496 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][OH:13])[CH:6]=[CH:5]2.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH:12]=[O:13])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 13473070(6-Bromonaphthalen-2-yl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 134770296-Bromonaphthalene-2-carbaldehydeYield 77.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a three-necked flask (250 ml) was added (6-bromonaphthalen-2-yl)methanol (40.0 g, 0.170 mol) and dichloromethane (1.6 L) with magnetic stirring under nitrogen to form a clear solution. To this solution, Pyridinium chlorochromate (40.0 g, 0.186 mol) was added, and the resulting mixture turned black at once. Stirring was continued for 1 hour. The mixture was filtered through a short silica gel column, eluted with dichloromethane; the filtrate was dried over anhydrous magnesium sulphate, and then filtered under reduced pressure. The solvent was removed to afford a light brown solid, which was recrystallized from ethanol-water solution (50%) to afford a white solid 6-bromo-2-naphthaldehyde (31 g).

Workup

  1. customto form a clear solution
  2. stirringStirring
  3. filtrationThe mixture was filtered through a short silica gel column
  4. washeluted with dichloromethane
  5. dry with materialthe filtrate was dried over anhydrous magnesium sulphate
  6. filtrationfiltered under reduced pressure
  7. customThe solvent was removed
  8. customto afford a light brown solid, which
  9. customwas recrystallized from ethanol-water solution (50%)

Sources & evidence

ORD record
ord-0a711edd7d3c4126a51d193ceb90d871
Source dataset
uspto-grants-2014_10
Patent number
US08872422B2

Reaction notes

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