ChemicalBook CAS DataBase List methyl 4-(bromomethyl)-2-methoxybenzoate

methyl 4-(bromomethyl)-2-methoxybenzoate synthesis

9synthesis methods

Product Name:methyl 4-(bromomethyl)-2-methoxybenzoate
CAS Number:74733-27-0
Molecular formula:C10H11BrO3
Molecular Weight:259.1

81245-24-1

74733-27-0

General procedure for the synthesis of methyl 4-bromomethyl-2-methoxybenzoate from methyl 2-methoxy-4-methylbenzoate: over a period of 1.5 h, bromine (6.19 mL, 120 mmol) was slowly added dropwise over a period of 1.5 h to a reflux mixture of methyl 2-methoxy-4-methylbenzoate (21.625 g, 120 mmol) in carbon tetrachloride (240 mL) dissolved in a carbon tetrachloride (75 mL). During the dropwise addition, the reaction mixture was irradiated using a 250W tungsten lamp. After dropwise addition, the reaction was continued at reflux for 15 minutes. Upon completion of the reaction, the mixture was concentrated and the solvent was removed under vacuum to afford methyl 4-bromomethyl-2-methoxybenzoate as an oily product (29.864 g, 96% yield). The product was confirmed by NMR hydrogen spectrum (400 MHz, CDCl3): δ 2.40 (s, 3H), 3.87 (s, 3H), 3.91 (s, 3H), 4.44 (s, 2H). Mass spectrometry (FIA-MS) showed the molecular ion peak m/e: 259 ([M+1]+).

81245-24-1 Synthesis

81245-24-1
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74733-27-0
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Yield: 96%

Reaction Conditions:

with bromine in tetrachloromethane for 1.75 h;Heating / reflux;Irradiation;

Steps:

73.B B. Methyl 2-Methoxy-4-(bromomethyl)benzoate
To a refluxing mixture of methyl 2-methoxy-4-methyl-benzoate (21.625 g, 120 mmol) in CC14 (240 mL) was addeddropwise a solution of bromine (6.19 mL, 120 mmol) in CC14(75 mL) over 1.5 h. During the bromine addition thereaction was irradiated with a 250 W tungsten lamp. Afterthe addition, the reaction was refluxed for 15 min andconcentrated, and vacuum pumped to give methyl 2-methoxy-4-(bromomethyl)benzoate as an oil (29.864 g, 96%)..NMR (400MHz, CDC1₃): 5 partial 2.40 (s, 3H), 3.87 (s, 3H),3.91 (s, 3H), 4.44 (s, 2H).FIA-MS, m/e: 259 (m+1).

References:

ELI LILLY AND COMPANY WO2004/108677, 2004, A1 Location in patent:Page 199