ChemicalBook CAS DataBase List ETHYL 2-(BROMOMETHYL)BENZOATE

ETHYL 2-(BROMOMETHYL)BENZOATE synthesis

9synthesis methods

Product Name:ETHYL 2-(BROMOMETHYL)BENZOATE
CAS Number:7115-91-5
Molecular formula:C10H11BrO2
Molecular Weight:243.1

87-24-1
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$14.00/1g

7115-91-5
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$29.00/100mg

Yield: 99%

Reaction Conditions:

with N-Bromosuccinimide;dibenzoyl peroxide in tetrachloromethane at 0; for 3.5 h;Heating / reflux;

Steps:

9
A solution of ethyl 2-toluate (17, 41.2 g, 0.25 mole) in carbon tetrachloride (200 mL) was added dropwise to a stirring mixture of benzoyl peroxide (100 mg), carbon tetrachloride (200 mL), and NBS (44.5 g, 0.25 mole) at 0° C. The mixture was heated at reflux for 3.5 hr under nitrogen, and allowed to cool to room temperature overnight. The precipitated succinimide was removed by filtration and the filter cake was washed with carbon tetrachloride. The combined filtrates were washed successively with 2 N NaOH (100 mL), and water (2*100 mL), and the solution was dried over anhydrous MgSO₄, filtered (Celite), and evaporated under vacuum to yield an oil. Drying under high vacuum overnight afforded 60.5 g (99%) of compound 18: ¹H NMR of the product showed the presence of ca. 15% of unreacted 17. The mixture was used in the next step without further purification: ¹H NMR (CDCl₃) δ 1.43 (t, J=7 Hz, 3H, CH₂ CH₃), 4.41 (q, J=7 Hz, 2H, CH₂CH₃), 4.96 (s, 1H, CH₂Br), 7.24 (m, 1H, ArH), 7.38 (m, 1H, ArH), 7.48 (m, 2H, ArH).

References:

DarPharma, Inc. US2007/155720, 2007, A1 Location in patent:Page/Page column 22

118-90-1 Synthesis