Methyl 3-(broMoMethyl)-6-chloropicolinate synthesis
- Product Name:Methyl 3-(broMoMethyl)-6-chloropicolinate
- CAS Number:1201924-34-6
- Molecular formula:C8H7BrClNO2
- Molecular Weight:264.5
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Yield: 68%
Reaction Conditions:
with N-Bromosuccinimide;acetic acid;dibenzoyl peroxide in tetrachloromethane at 100; for 1 h;
Steps:
F.6.IV.a PREPARATION OF METHYL 3-(BROMOMETHYL)-6-CHLOROPICOLINATE
[00486] To a flask containing a magnetic stir bar was added methyl 6-chloro-3- methylpicolinate (750 mg, 4.04 mmol, 1.0 eq.), followed by CC (15.0 mL). To this mixture was added N-bromosuccinimide (1.44 g, 8.08 mmol, 2.0 eq.), benzoyl peroxide (29.4 mg, 0.12 mmol, 0.03 eq.), and acetic acid (231 μ, 4.04 mmol, 1.0 eq.). The reaction mixture was stirred at 100 °C for 1 hour. The reaction mixture was cooled to room temperature and quenched with saturated aquesous NH4.CI solution (10 mL). The mixture was extracted with CH2CI2 (3x). The organic layers were combined, dried over Na2SC>4, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to provide the desired compound as a solid (735 mg, 68%). ES-MS [M+l]+: 265.8.
References:
VANDERBILT UNIVERSITY;BENDER, Aaron, M.;CONN, P., Jeffrey;LINDSLEY, Craig, W.;EMMITTE, Kyle, A.;HAN, Changho;ENGERS, Julie, L. WO2016/172547, 2016, A1 Location in patent:Paragraph 00486
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