| Identification | Back Directory | [Name]
Methyl 2-bromo-3-methylbenzoate | [CAS]
131001-86-0 | [Synonyms]
Methyl 2-bromo-3-met
METHYL 2-BROMO-3-METHYLBENZOATE
Methyl 3-Methyl-2-Bromobenzoate
2-Bromo-m-toluic acid methyl ester
Methyl 2-Bromo-3-Methoxynicotinate
2-BROMO-3-METHYL-BENZOIC ACID METHYL ESTER
2-Bromo-m-toluic acid methyl ester (COOCH3=1)
Benzoic acid, 2-bromo-3-methyl-, methyl ester | [Molecular Formula]
C9H9BrO2 | [MDL Number]
MFCD00144762 | [MOL File]
131001-86-0.mol | [Molecular Weight]
229.07 |
| Chemical Properties | Back Directory | [Boiling point ]
267.4±20.0 °C(Predicted) | [density ]
1.433±0.06 g/cm3(Predicted) | [refractive index ]
1.5530 to 1.5570 | [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
Liquid | [color ]
Red | [Water Solubility ]
Slightly soluble in water. | [CAS DataBase Reference]
131001-86-0 |
| Hazard Information | Back Directory | [Chemical Properties]
brown liquid | [Uses]
Methyl 2-bromo-3-methylbenzoate is used as pharmaceutical intermediate. | [Synthesis]
A mixed solution of 2-bromo-3-methylbenzoic acid (5 g, 23.2 mmol) and concentrated sulfuric acid (0.5 mL) in anhydrous methanol (100 mL) was heated to reflux for 20 hours. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure by rotary evaporator. The concentrated residue was dissolved in dichloromethane (50 mL) and washed with saturated sodium bicarbonate solution (30 mL) to neutralize the acid. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated again under reduced pressure by rotary evaporator to afford methyl 2-bromo-3-methylbenzoate (4.43 g, 19.3 mmol, 83% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 2.46 (s, 3H), 3.93 (s, 3H), 7.24 (t, J = 8.0 Hz, 1H), 7.34 (dd, J = 1.0 Hz, J = 8.0 Hz, 1H), 7.46 (dd, J = 1.0 Hz, J = 8.0 Hz, 1H). | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 2, p. 644 - 651
[2] Journal of the American Chemical Society, 2016, vol. 138, # 18, p. 5813 - 5816
[3] Patent: WO2004/37806, 2004, A1. Location in patent: Page 45
[4] Patent: WO2018/205948, 2018, A1. Location in patent: Page/Page column 49
[5] Patent: WO2004/37806, 2004, A1. Location in patent: Page 71 |
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