Dimethylformamide → HCID 68585664, compound

Participants

Reaction Steps

A solution of 1-methoxy-3-nonyl benzene (7.5 g; 32 mmol) in DMF (60 mL) was cooled to −10° C. and N-bromosuccinimide (5.42 g; 30 mmol) was added under stirring over 30 minutes. The MeOH/ice bath was removed after 1 hour and the reaction mixture was left overnight with stirring. The reaction mixture was poured onto H2O (100 mL) and 10 M NaOH (aq) was added. The alkaline slurry was extracted with EtOAc (2×) and the combined organic fractions washed with 1 M NaOH (aq.; 2×), dried (MgSO4), filtered and evaporated to dryness. The crude product was further purified by column chromatography (SiO2; EtOAc/PE80-100° C.=0:1→1:20) to yield 9.8 g (quantitative) of product with satisfactory purity.

Provenance & Evidence