| Identification | Back Directory | [Name]
Methyl 3-broMo-4-forMylbenzoate | [CAS]
90484-53-0 | [Synonyms]
ethyl 3-broMo-4-forMylbenzoate
Methyl 3-broMo-4-forMylbenzoate
3-Bromo-4-formyl-benzoic acid methyl ester
Benzoic acid, 3-bromo-4-formyl-, methyl ester | [Molecular Formula]
C9H7BrO3 | [MDL Number]
MFCD16036864 | [MOL File]
90484-53-0.mol | [Molecular Weight]
243.05 |
| Chemical Properties | Back Directory | [Melting point ]
76.8-77.6℃ | [Boiling point ]
326.0±27.0 °C(Predicted) | [density ]
1.566±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [form ]
crystalline solid | [color ]
Off-white/faint yellow | [InChI]
InChI=1S/C9H7BrO3/c1-13-9(12)6-2-3-7(5-11)8(10)4-6/h2-5H,1H3 | [InChIKey]
OILDTPUIIUEPFL-UHFFFAOYSA-N | [SMILES]
C(OC)(=O)C1=CC=C(C=O)C(Br)=C1 |
| Hazard Information | Back Directory | [Synthesis]
General procedure for the synthesis of methyl 3-bromo-4-(dibromomethyl)benzoate from methyl 3-bromo-4-(dibromomethyl)benzoate: To a solution of methyl 3-bromo-4-(dibromomethyl)benzoate (32.0 g, 65.3 mmol) in acetone (400 mL) was added silver nitrate (33.3 g, 196 mmol) and water (100 mL). The reaction mixture was stirred at room temperature for 1 hour away from light. Upon completion of the reaction, the resulting silver salt was removed by filtration and the filtrate was diluted with ethyl acetate and washed sequentially with brine, saturated sodium bicarbonate solution and water. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure and purified by silica gel column chromatography (eluent: ethyl acetate/hexane, 0-20% gradient) to afford methyl 3-bromo-4-formylbenzoate (12.9 g, 52.0 mmol, 80% yield) as a white solid. The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6) and LC/MS: 1H NMR δ 10.26 (s, 1H), 8.23 (s, 1H), 8.08 (d, J = 8.1 Hz, 1H), 7.97 (d, J = 8.0 Hz, 1H), 3.91 (s, 3H); LC/MS (m/z) ES: 243 ( M+1). | [References]
[1] Tetrahedron, 2008, vol. 64, # 4, p. 688 - 695
[2] Patent: WO2017/2078, 2017, A1. Location in patent: Page/Page column 37; 38
[3] European Journal of Medicinal Chemistry, 2015, vol. 92, p. 818 - 838
[4] Patent: WO2013/149997, 2013, A1. Location in patent: Page/Page column 50; 51
[5] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2016, vol. 55B, # 7, p. 854 - 881 |
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