1-Chloromethylnaphthalene → HCID 86643579, compound

Participants

Reaction Conditions

Reaction Steps

The corresponding Grignard compound is prepared from 88.3 g (500 mmol) of 1-chloromethylnaphthalene and 12.2 g (500 mmol) of magnesium in 500 ml of ether. After the Grignard solution has been cooled to −78° C., 59 ml (530 mmol) of trimethyl borate are added, the mixture is then allowed to warm to room temperature, the solvent is removed in vacuo, 500 ml of toluene, 92.5 g (500 mmol) of 2-bromobenzaldehyde, 2.9 g (2.5 mmol) of tetrakis(triphenylphosphino)palladium(0) and 300 ml of 2 M sodium carbonate solution are added to the residue, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, washed twice with 500 ml of water each time, filtered through silica gel and then evaporated to dryness, and the residue is recrystallised from toluene/acetonitrile. Yield: 93.1 g (378 mmol), 75.6%, purity about 97% (NMR).

Provenance & Evidence