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103347-14-4

103347-14-4 Structure

103347-14-4 Structure
IdentificationBack Directory
[Name]

4-(bromomethyl)-1-chloro-2-methoxybenzene
[CAS]

103347-14-4
[Synonyms]

4-Chloro-3-Methoxybenzyl broMide
4-(bromomethyl)-1-chloro-2-methoxybenzene
Benzene, 4-(bromomethyl)-1-chloro-2-methoxy-
[Molecular Formula]

C8H8BrClO
[MDL Number]

MFCD09907927
[MOL File]

103347-14-4.mol
[Molecular Weight]

235.51
Chemical PropertiesBack Directory
[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 DataBack Directory
[Symbol(GHS) ]


GHS05
[Signal word ]

Danger
[Hazard statements ]

H314
[Precautionary statements ]

P260-P280
[HS Code ]

2909309090
Hazard InformationBack Directory
[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]

4-chloro-3-methoxytoluene

73909-16-7

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

103347-14-4

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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