Bromomethyl methyl ether → 1-Bromo-4-chloro-2-fluoro-3-(methoxymethyl)benzene

Temperatur

-20 °C

A solution of 1-bromo-4-chloro-2-fluorobenzene (20.4 g, 0.100 mol) in THF (50 mL) was slowly added to LDA (0.125 mol) in THF (600 mL) at −50° C. After addition the solution was warmed to −20° C. and then cooled to −50° C. a solution of bromomethoxymethane (25 g, 0.200 mol) in THF (25 mL) was slowly added and the reaction mixture was warmed to ambient temperature. The reaction was quenched with water (400 mL) and extracted with diethyl ether (2×150 mL). The combined organic phases were dried (sodium sulfate) and concentrated. The residual oil was distilled (70°-75° C./0.5 mm) to give 1-bromo-4-chloro-2-fluoro-3-methoxymethylbenzene (18.0 g, 0.071 mol): 1H NMR (CDCl3): δ 7.50 (m, 1H), 7.15 (dd, 1H), 4.65 (s, 1H), 3.40 (s, 1H).

1. additionAfter addition the solution
2. additionwas slowly added
3. temperaturethe reaction mixture was warmed to ambient temperature
4. customThe reaction was quenched with water (400 mL)
5. extractionextracted with diethyl ether (2×150 mL)
6. dry with materialThe combined organic phases were dried (sodium sulfate)
7. concentrationconcentrated
8. distillationThe residual oil was distilled (70°-75° C./0.5 mm)

ORD-Eintrag

ord-ac2da014daba480d85a8943209a2482b

Quelldatensatz

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07314849B2