Diethyl Ether → HCID 63492680, compound

Participants

Reaction Conditions

Reaction Steps

To an oven-dried three-neck round bottom flask fitted with a condenser and addition funnel charged flushed with nitrogen was added magnesium (2.82 g; 116 mmol) and anhydrous ether (100 mL). A solution of 4-methylbenzyl bromide (12.91 g; 69.7 mmol) in ether (50 mL) was added dropwise via the addition funnel at room temperature. After the addition, the reaction mixture was heated at 40° C. for 2 hours. The reaction mixture was allowed to cool to room temperature and was cannulated to another dried flask charged with a solution of 2,4-dichlorobenzonitrile (10.0 g; 58.0 mmol) in ether (150 mL) under a nitrogen atmosphere. The resulting reaction mixture was stirred at 40° C. for 6 hours. The reaction was cooled to room temperature and quenched slowly with 2N aq. HCl. Partitioned between ethyl acetate and 2N aq. HCl. The organic portion was washed with 2N aq. HCl, water, brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was filtered through a silica gel plug (eluted with 20% ethyl acetate/hexane), and recrystallized from hexane to afford product: m/e=279 (M+1).

Provenance & Evidence