| Identification | Back Directory | [Name]
METHYL 2-BROMOMETHYL-5-CHLORO-BENZOATE | [CAS]
668262-52-0 | [Synonyms]
-5-chlorobenzoate
METHYL 2-BROMOMETHYL-5-CHLORO-BENZOATE
2-BROMOMETHYL-5-CHLORO-BENZOIC ACID METHYL ESTER
2-carboxy-4-chloro-broMoMethylbenzene Methyl ester
Benzoic acid, 2-(bromomethyl)-5-chloro-, methyl ester | [Molecular Formula]
C9H8BrClO2 | [MDL Number]
MFCD06804577 | [MOL File]
668262-52-0.mol | [Molecular Weight]
263.52 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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