|
|
| | METHYL 2-BROMOMETHYL-5-CHLORO-BENZOATE Basic information |
| Product Name: | METHYL 2-BROMOMETHYL-5-CHLORO-BENZOATE | | Synonyms: | METHYL 2-BROMOMETHYL-5-CHLORO-BENZOATE;Benzoic acid, 2-(bromomethyl)-5-chloro-, methyl ester;2-BROMOMETHYL-5-CHLORO-BENZOIC ACID METHYL ESTER;2-carboxy-4-chloro-broMoMethylbenzene Methyl ester;-5-chlorobenzoate;2-(bromethyl)-5-chloromethyl benzoate | | CAS: | 668262-52-0 | | MF: | C9H8BrClO2 | | MW: | 263.52 | | EINECS: | | | Product Categories: | | | Mol File: | 668262-52-0.mol |  |
| | METHYL 2-BROMOMETHYL-5-CHLORO-BENZOATE Chemical Properties |
| Boiling point | 331.0±32.0 °C(Predicted) | | density | 1.561±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | form | liquid | | color | Yellow |
| | METHYL 2-BROMOMETHYL-5-CHLORO-BENZOATE Usage And Synthesis |
| Synthesis | General procedure for the synthesis of methyl 2-(bromomethyl)-5-chlorobenzoate from methyl 2-methyl-5-chlorobenzoate: methyl 5-chloro-2-methylbenzoate (10.0 g, 54 mmol), N-bromosuccinimide (NBS, 10.6 g, 59.5 mmol), and azobisisobutyronitrile (AIBN, 200 mg) were dissolved in 1,2-dichloroethane ( 300 mL). The reaction mixture was irradiated and stirred for 2 h under photocatalytic conditions using [PHOTOLAMP]. Upon completion of the reaction, the mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with heptane/dichloromethane as eluent (gradient elution: 9:1, 4:1, 1:1) to afford 11.8 g of methyl 2-(bromomethyl)-5-chlorobenzoate (83% yield). The product was characterized by 1H NMR (300 MHz, CDCl3): δ 7.98 (d, J = 2.1 Hz, 1H), 7.49 (dd, J = 2.2, 8.2 Hz, 1H), 7.43 (d, J = 8.2 Hz, 1H), 4.93 (s, 2H), 3.97 (s, 3H). | | References | [1] Patent: WO2004/18414, 2004, A2. Location in patent: Page 112
[2] Patent: WO2005/21508, 2005, A1. Location in patent: Page/Page column 148
[3] Israel Journal of Chemistry, 1971, vol. 9, p. 111 - 118
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 5, p. 1628 - 1631
[5] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 360 - 365 |
| | METHYL 2-BROMOMETHYL-5-CHLORO-BENZOATE Preparation Products And Raw materials |
|