1-Fluoronaphthalene → 4-Fluoronaphthalene-1-carbaldehyde

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Reaction Steps

SnCl4 (13 ml, 1M solution in dichloromethane) is added to a solution of dichlormethyl-methylether in dichloromethane (6 ml) at 0° C. After 1 hour at 0° C., a solution of 1-fluoro-naphtalene (1.46 g) in dichloromethane (4 ml) is added over 10 minutes. The reaction is stirred overnight at room temperature and then quenched with cold water (30 ml). The organic phase is separated and the aqueous phase is extracted 3 times with dichloromethane. The combined organic phases are dried over Na2SO4 and concentrated in vacuo to yield 4-fluoro-naphthalene-1-carbaldehyde (1.73 g, dark brown crystals). The crude product obtained is used without further purification, MS (HPLC/MS): no ionisation. Retention time: 3.88 min.

Provenance & Evidence