1-Fluoronaphthalene → 4-Fluoronaphthalene-1-carbaldehyde

Participants

Reaction Steps

A solution of α,α-dichloromethyl methyl ether (5.9 mL, 65 mmol) in CH2Cl2 (30 mL) was cooled in an ice bath and then treated dropwise over 15 min with SnCl4 (7.6 mL, 65 mmol). After stirring for 45 min, a solution of 1-fluoronaphthalene (5.5 mL, 50 mmol) in CH2Cl2 (30 mL) was added. The mixture was allowed to slowly warm to room temperature while stirring overnight. The mixture was poured in ice water (100 mL) and diluted with CH2Cl2 (50 mL). The layers were separated. The organic layer was diluted with CH2Cl2 (100 mL), washed with H2O (3×50 mL), dried over Na2SO4, filtered, and the solvent was removed in vacuo to give the title compound (7.62 g, 87%) as a pale yellow solid: MS (ESI) m/e 175 (M+H)+.

Provenance & Evidence