4-(bromomethyl)-1-chloro-2-methoxybenzene Chemical Properties

Boiling point:

115 °C(Press: 0.4 Torr)

Density 

1.520±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Dichloromethane, Ethyl Acetate

form 

Oil

color 

Pale Yellow

Safety Information

HS Code 

2909309090

4-(bromomethyl)-1-chloro-2-methoxybenzene Usage And Synthesis

Uses

4-(Bromomethyl)-1-chloro-2-methoxybenzene is an intermediate in the synthesis of 5-(3-((1H-1,2,4-Triazol-1-yl)methyl)-3-hydroxy-4,4-dimethylpentyl)-2-chlorophenol (T767575), which is a tebuconazole impurity. Tebuconazole (T013000) is an ergosterol biosynthesis inhibitor. Fungicide.

Synthesis

General procedure for the synthesis of 4-(bromomethyl)-1-chloro-2-methoxybenzene from 1-chloro-2-methoxy-4-methylbenzene: to a solution of 1-chloro-2-methoxy-4-methylbenzene (274 g, 1.75 mol) in dichloromethane (2.5 L) was added benzoyl peroxide (4.23 g, 0.02 mol) and N-bromosuccinimide (NBS. 321 g, 1.80 mol). The reaction mixture was heated to reflux for 1 h under mechanical stirring. After completion of the reaction, the reaction mixture was cooled, washed sequentially with 1N hydrochloric acid (2L), saturated sodium bicarbonate solution (2L) and brine (2L), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford 4-(bromomethyl)-1-chloro-2-methoxybenzene as a pale yellow solid (412 g, quantitative yield).1H NMR (400 MHz, CDCl3): δ7.30- 7.34 (d, 1H), 6.95 (s, 1H), 6.91-6.93 (d, 1H), 4.45 (s, 2H), 3.92 (s, 3H).

References

[1] Patent: WO2011/71565, 2011, A1. Location in patent: Page/Page column 145-146
[2] Patent: WO2010/93845, 2010, A1. Location in patent: Page/Page column 136-137
[3] Patent: US6984657, 2006, B1
[4] Patent: US2007/244159, 2007, A1. Location in patent: Page/Page column 91
[5] Patent: US2011/98311, 2011, A1

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