Methyl 2-bromomethyl-3-methoxybenzoate

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Methyl 2-bromomethyl-3-methoxybenzoate Basic information
Product Name:Methyl 2-bromomethyl-3-methoxybenzoate
Synonyms:METHYL 2-BROMOMETHYL-3-METHOXY-BENZOATE;2-Bromomethyl-3-methoxybenzoic acid methyl ester;Benzoic acid, 2-(bromomethyl)-3-methoxy-, methyl ester;2-bromethyl-3-methoxymethyl benzoate
CAS:71887-28-0
MF:C10H11BrO3
MW:259.1
EINECS:
Product Categories:
Mol File:71887-28-0.mol
Methyl 2-bromomethyl-3-methoxybenzoate Structure
Methyl 2-bromomethyl-3-methoxybenzoate Chemical Properties
Melting point 112-114 °C(Solv: hexane (110-54-3))
Boiling point 330.0±32.0 °C(Predicted)
density 1.432
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
AppearanceWhite to off-white Solid
Safety Information
MSDS Information
Methyl 2-bromomethyl-3-methoxybenzoate Usage And Synthesis
Synthesis
Methyl 3-methoxy-2-methylbenzoate

42981-93-1

Methyl 2-bromomethyl-3-methoxybenzoate

71887-28-0

General procedure for the synthesis of methyl 2-bromomethyl-3-methoxybenzoate from methyl 3-methoxy-2-methylbenzoate: to a solution of CHCl3 (2-5 mL/mmol) or CCl4 (5 mL/mmol) containing methyl 3-methoxy-2-methylbenzoate (1.00 eq.), N-bromosuccinimide (NBS, 1.10- 2.20 eq.) and azobisisobutyronitrile (AIBN, 0.02-0.04 eq.). The reaction mixture was heated to reflux for 2-22 hours and subsequently cooled to room temperature. Upon completion of the reaction, the solvent is removed by evaporation under reduced pressure if CHCl3 is used as solvent, or by distillation if CCl4 is used, to give the target product methyl 2-bromomethyl-3-methoxybenzoate. Precautions: CHCl3 and CCl4 are highly toxic and carcinogenic, protective gloves should be worn and the operation should be carried out in a fume hood.

References[1] Tetrahedron, 2018, vol. 74, # 2, p. 224 - 239
[2] Journal of Organic Chemistry, 1980, vol. 45, # 1, p. 12 - 15
[3] Patent: WO2004/26875, 2004, A1. Location in patent: Page 38
[4] Patent: US2004/106791, 2004, A1. Location in patent: Page 9
[5] Chinese Chemical Letters, 2012, vol. 23, # 1, p. 9 - 12
Methyl 2-bromomethyl-3-methoxybenzoate Preparation Products And Raw materials
Raw materialsMethyl 3-methoxy-2-methylbenzoate-->Chloroform-->N-Bromosuccinimide-->AIBN
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