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

HRID 446210Notes

Reaction equation

HRID 446210 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Br:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([CH2:23][OH:24])[CH:17]=[CH:16]2>ClCCl>[Br:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([CH:23]=[O:24])[CH:17]=[CH:16]2

Participants

4

Reactant 2

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

Product 1

HCID 134770296-Bromonaphthalene-2-carbaldehydeYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridinium chlorochromate (7.8 g, 36.3 mmol), 4 Å molecular sieve (9.1 g), and purified dichloromethane (100 mL) were put into a reaction vessel under a nitrogen atmosphere, a solution prepared by dissolving (6-bromonaphthalene-2-yl)methanol (4.3 g, 18.1 mmol) in purified dichloromethane (100 mL) was slowly added thereto at 0° C. The reaction mixture solution was stirred at room temperature for 1 hour, and then was filtered using silica gel. After the solvent was removed, the filtered material was dried in vacuum to thereby obtain a white solid (4.0 g, yield: 94%).

Workup

  1. customwere put into a reaction vessel under a nitrogen atmosphere
  2. customa solution prepared
  3. additionwas slowly added
  4. customat 0° C
  5. filtrationwas filtered
  6. customAfter the solvent was removed
  7. customthe filtered material was dried in vacuum

Sources & evidence

ORD record
ord-f47f910a07b54ec6897862f5f3508b9d
Source dataset
uspto-grants-2013_07
Patent number
US08476474B2

Reaction notes

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