Butyl bromide → HCID 17993053, compound

Participants

Reaction Steps

To a stirred suspension of sodium hydride (NaH) (2.63 grams, 66 mmol, 60 percent dispersion in oil) in anhydrous N,N-dimethylformamide (DMF) (15 milliliters) was added dropwise a solution of 3-thiophenemethanol (5.105 grams, 43.8 mmol) in DMF (15 milliliters). The reaction mixture was stirred until the evolution of hydrogen ceased (about 0.5 hour). To the resulting suspension, 1-bromobutane (10.3 grams, 75 mmol) in DMF (15 milliliters) was added dropwise and then stirred at room temperature for 4 hours. The reaction mixture was poured into water (200 milliliters) and extracted with ether/hexane (v/v, 100 milliliters/100 milliliters), and washed with brine. The resulting organic layer was dried over magnesium sulfate (MgSO4) and filtered. After removing the DMF solvent, a light yellow liquid was obtained, which was subjected to column chromatography on a silica gel using first hexane (about 400 milliliters to remove mineral oil), and then hexane/CH2Cl2(dichloromethane) (v/v=1/1; 1,200 milliliters). After evaporating the solvents, a colorless liquid was obtained.

Provenance & Evidence