1-Fluoronaphthalene → 4-Fluoronaphthalene-1-carbaldehyde

HRID 1889289Notes

Reaction equation

HRID 1889289 reaction equation
C[O:2][CH:3](Cl)Cl.[Sn](Cl)(Cl)(Cl)Cl.[F:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1>ClCCl>[F:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH:3]=[O:2])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 94501-FluoronaphthaleneHCID 21004Methane, dichloromethoxy-HCID 24287Tin tetrachloride

Product 1

HCID 70225244-Fluoronaphthalene-1-carbaldehydeYield 100.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

19.9 g Dichloromethyl methyl ether and 45.7 g tin chloride were dissolved in 70 ml dichloromethane. The solution was cooled to +5° C. and 20.0 g fluoronapthalene in dichloromethane (49 ml) was added over a 60 min period, while keeping the temperature at 5° C. The reaction was brought to room temperature after the addition. After 4 h the reaction was quenched by slowly pouring it into an ice/water mixture. This mixture was stirred for 15 min and left standing overnight. The dichloromethane layer was washed with water, dried (sodium sulfate), filtered through celite and concentrated in vacuo to obtain 24.0 g of 4-fluoro-naphthalene-1-carbaldehyde as an off white solid.

Workup

  1. temperatureThe solution was cooled to +5° C.
  2. customat 5° C
  3. customwas brought to room temperature
  4. additionafter the addition
  5. customAfter 4 h the reaction was quenched
  6. additionby slowly pouring it into an ice/water mixture
  7. waitleft
  8. waitstanding overnight
  9. washThe dichloromethane layer was washed with water
  10. dry with materialdried (sodium sulfate)
  11. filtrationfiltered through celite and
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-febdf8d1b280446194848100dda26a68
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

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