Diethyl Ether → 6-Bromonaphthalene-2-carbaldehyde

HRID 860528Notes

Reaction equation

HRID 860528 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.CCOCC>C(Cl)Cl>[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

5

Reactant 3

HCID 3283Diethyl EtherHCID 13473070(6-Bromonaphthalen-2-yl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 134770296-Bromonaphthalene-2-carbaldehydeYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-bromo-2-naphthylmethyl alcohol (6.71 g, 28.3 mmol) in CH2Cl2 (350 mL) was added pyridinium chlorochromate (6.71 g, 31.13 mmol) all at once. The mixture visually went from orange-red to black over 30 minutes and 150 mL of ether was added. The black mixture was passed through a silica gel column and eluted with ether. The solvents were evaporated and the solid was further purified on silica gel (hexane:CH2Cl2 1:1) to give 6.25 g of 6-bromo-2-naphthaldehyde (94%) as a white solid. %). 1H NMR (300 MHz; CDCl3): δ 7.65 (dd, J1=2.0 Hz, J2=9.0 Hz, 1H); 7.84 (t, J=8.0 Hz, 2H); 7.97 (dd, J1=2.0 Hz, J2=8.0 Hz, 1H); 8.06 (d, J=2.0 Hz, 1H); 8.29 (s, 1H); 10.14 (s, 1H); 13C NMR (300 MHz; CDCl3): ppm 123.5, 123.9, 128.0, 130.1, 130.5, 130.8, 130.9, 133.9, 134.2, 137.1, 191.6.

Workup

  1. washeluted with ether
  2. customThe solvents were evaporated
  3. customthe solid was further purified on silica gel (hexane:CH2Cl2 1:1)

Sources & evidence

ORD record
ord-1f52b8b8d8874260bc0cd4919ff16384
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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