2-FLUOROBENZYLZINC CHLORIDE synthesis
- Product Name:2-FLUOROBENZYLZINC CHLORIDE
- CAS Number:312693-05-3
- Molecular formula:C7H6ClFZn
- Molecular Weight:209.95
58481-11-1
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312693-05-3
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$190.00/50ml
1251844-70-8
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Yield:1251844-70-8 73%
Reaction Conditions:
tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran at 60; for 18 h;Inert atmosphere;
Steps:
45.1
Methyl 2-chloroisonicotinate (5.2 g, 30.31 mmol) and Pd(PPh3)4 (0.700 g, 0.61 mmol) were dissolved under nitrogen in THF (100 mL) and (2-fluorobenzyl)zinc(II) chloride (0.5 M in THF) (90 mL, 45.00 mmol) was added and the brown solution was stirred at 60° C. for 18 h. The reaction was quenched by addition of methanol (50.0 mL). The solution was diluted with EtOAc, washed with NH4Cl (aq) and dried over Na2SO4, then evaporated. The compound was purified in 2 runs via Biotage, SNAP 340 g KP-SIL, eluent isocratic heptane/ethyl acetate 8:2 for 2 CV, then linear gradient heptane/ethyl acetate 8:2 to 5:5 over 5 CV to give methyl 2-(2-fluorobenzyl)isonicotinate (5.42 g, 73%) as a yellow oil. 1H NMR (400 MHz, cdcl3) 3.92 (s, 3H), 4.25 (s, 2H), 7.00-7.13 (m, 2H), 7.18-7.30 (m, 2H), 7.64-7.74 (m, 2H), 8.69 (d, 1H). MS m/z 246 (M+H)+
References:
US2010/261755,2010,A1 Location in patent:Page/Page column 39
312693-05-3
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$190.00/50ml
2719-27-9
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636597-75-6
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