3-(Bromomethyl)thiophene → HCID 54352789, compound

Participants

Reaction Steps

A solution of 3(bromomethyl)thiophene (6.2 g, 0.035 mol) in carbon tetrachloride (25 ml) was added to a solution of sodium methoxyethoxide (8.9 g, 0.09 mol) in methoxyethanol (90 ml) and the mixture was heated under reflux for 2 hours. After cooling to room temperature, the solvent mixture was removed under reduced pressure and the resultant oil was dissolved in dichloromethane (100 ml), extracted with distilled water (2×100 ml) and dried over potassium carbonate. After removal of the solvent, the crude oil was distilled under reduced pressure to yield 3-(methoxyethoxymethyl)thiophene (3.0 g, 50%), B.p. 100°-101° C./10 mm Hg. (Found: C, 55.0; H, 6.3; S, 17.6. Calculated for C8H12O2S: C, 55.8; H, 7.0; S, 18.6%); EI m/e Intensity (%): 172 (5, M+), 97 (12, C4H3S.CH2); δH(CDCl3): 7.05-7.24 (3H, m), 4.53 (2H, s), 3.54 (4H, m) and 3.34 (3H, s); δC(CDCl3): 59.6, 67.0, 69.7, 72.5, 123.4, 126.5, 127.9, 140.0 ppm.

Provenance & Evidence