1-Bromo-2-methylpropane → HCID 22149719, compound

Participants

Reaction Steps

In a 3 necked round bottom flask (100 ml), equipped with a dropping funnel reflux condenser and thermometer pocket, placed magnesium turnings (1.45 gm 0.0604 mole) and flame dried the apparatus. Dry diethyl ether (15 ml.) was added to Mg. Turning, Isobutyl bromide (6.57 ml, 8.28 gm, 0.0645 mole) was taken in 5 ml of dry ether and added drop wise to the Mg turnings. As soon as ether starts boiling (in a few minutes) the reaction was cooled using ice-salt and continued the addition of isobutyl bromide. After complete addition of isobutyl bromide continued for another 20 minutes. o-Fluro benzaldehyde (4.25 ml, 5.0 gm, 0.0403 mole) in 10 ml of ether was added drop wise at −10° C. (around ½ hr). After the completion of addition of fluoro benzaldehyde continued the stirring for 1 hr and the reaction was quenched with ice-cooled saturated ammonium chloride solution (30 ml), the solid separated is filtered off, the filtrate is extracted with ethyl acetate (20×1, 10×2 ml) dried over sodium sulphate and concentrated to yield 6.54 gm of crude product (GC showed area of 85% purity). The crude product on vacuum distillation gave 3.93 gm (54.2%) of pure 3-methyl-1-(2-fluoro phenyl)butylalcohol (12) and impure product ˜2.87 gm containing 3-methyl-1-(2-fluoro phenyl)butylalcohol (12) 60% and byproduct (o-fluoro benzylalcohol) 40%. 1HNMR CDCl3 (spectrum 11): 0.96(d, 6H), 1.55(m, 1H), 1.75(m, 2H), 1.95 (bs, 1H), 5.05(m, 1H), 7.0(m, 1H), 7.20(m, 2H), 7.45(m, 1H)

Provenance & Evidence