Iodine → Stannane, tributyl(2-methoxy-4-methylphenyl)-

Temperature

50 °C

A solution of 2-bromo-5-methylanisole (3.8 g) [obtained as described in J. Gen. Chem. U.S.S.R., 1932, 2, 455 (Chemical Abstracts, 1933, 27, 962)] in THF (50 ml) was added to magnesium turnings (0.47 g) and a catalytic amount of iodine under an atmosphere of argon. A catalytic volume of 1M methyl magnesium bromide in ether was added and the mixture was heated 50° C. for 1 hour, and then cooled to 0° C. Tributyltin chloride (5.6 g) was added dropwise over 5 minutes and the mixture was stirred for 18 hours. Volatile material was removed by evaporation and the residue partitioned between ether (50 ml) and saturated ammonium chloride solution (50 ml). The organic phase was separated and washed with saturated ammonium chloride solution (2×20 ml). The ether layer was separated, diluted with ethyl acetate (50 ml), and washed with water (25 ml), followed by saturated sodium chloride solution (50 ml). Volatile material was removed by evaporation and the residue purified by distillation to give (2-methoxy-4-methylphenyl)tributyl tin (B) (4.8 g), as an oil, b.p. 190° C. at 0.05 torr; NMR: 0.75-1.7 (complex m,27H), 2.4(s,3H), 3.8(s,3H), 6.6(t,1H), 6.8(d,1H), 7.2(d,1H).

1. temperaturecooled to 0° C
2. customVolatile material was removed by evaporation
3. customthe residue partitioned between ether (50 ml) and saturated ammonium chloride solution (50 ml)
4. customThe organic phase was separated
5. washwashed with saturated ammonium chloride solution (2×20 ml)
6. customThe ether layer was separated
7. additiondiluted with ethyl acetate (50 ml)
8. washwashed with water (25 ml)
9. customVolatile material was removed by evaporation
10. distillationthe residue purified by distillation

ORD record

ord-33ad7c062421471d859b7077666ca3b9

Source dataset

uspto-grants-1995_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05444071