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ChemicalBook CAS DataBase List METHYL 2-BROMO-5-METHYLBENZOATE

METHYL 2-BROMO-5-METHYLBENZOATE synthesis

6synthesis methods

Product Name:METHYL 2-BROMO-5-METHYLBENZOATE
CAS Number:90971-88-3
Molecular formula:C9H9BrO2
Molecular Weight:229.07

67-56-1 Synthesis

67-56-1
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$7.29/5ml-f

6967-82-4 Synthesis

6967-82-4
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$6.00/1g

90971-88-3
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$6.00/1g

Yield: 99%

Reaction Conditions:

Stage #1:2-bromo-5-methylbenzoic acid with oxalyl dichloride;N,N-dimethyl-formamide in dichloromethane at 0 - 20; for 1 h;
Stage #2:methanol in dichloromethane at 20; for 3 h;

Steps:

4.3.1 Methyl 2-bromo-5-methylbenzoate (5)⁸
To a suspension of compound 4 (2.15 g, 10 mmol) in dry DCM (40 mL) and DMF (0.2 mL) at 0 °C was slowly added oxalyl chloride (1.3 mL, 15 mmol). After being stirred for 1 h at room temperature, the reaction mixture was treated with MeOH (20 mL) and then stirred for 3 h. The resulting solution was neutralized with saturated aqueous Na₂CO₃ (100 mL) and extracted with DCM (70 mL×2). The combined organic layer was washed with water (50 mL) and brine (50 mL), dried over anhydrous Na₂SO₄. The solvent was removed under reduced pressure and the residue was purified by chromatography on silica gel, eluting with petroleum ether/ethyl acetate (30:1), to afford compound 5 (2.27 g) as colorless oil in 99% isolated yield. ¹H NMR (CDCl₃, 400 MHz) δ 2.30 (s, 3H), 3.90 (s, 3H), 7.10 (dd, J=2.4, 8.4 Hz, 1H), 7.49 (d, J=8.0 Hz, 1H), 7.57 (d, J=2.0 Hz, 1H); ¹³C NMR (CDCl₃, 100 MHz) δ 20.7, 52.4, 118.2, 131.7, 131.9, 133.5, 134.1, 137.3, 166.8.

References:

Guo, Shenghai;Wang, Jiliang;Li, Yan;Fan, Xuesen [Tetrahedron,2014,vol. 70,# 14,p. 2383 - 2388]