2-methyl-5-chlorobenzyl chloride synthesis
- Product Name:2-methyl-5-chlorobenzyl chloride
- CAS Number:34060-72-5
- Molecular formula:C8H8Cl2
- Molecular Weight:175.06
58966-29-3
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Yield:34060-72-5 87%
Reaction Conditions:
with thionyl chloride in toluene at 10; for 0.5 h;
Steps:
A solution of 2-(benzyloxy)-4-hydroxy-6-methylnicotinate (Cpd LL, 18.0 g, 115 mmol) in anhydrous toluene (300 mL) was cooled to below 10° C. internal. Thionyl chloride (21.3 g, 179 mmol) was added dropwise, slowly enough to maintain the internal temperature below 10° C. The mixture was stirred at this temperature for 30 minutes, then the cooling bath was removed and stirring continued at room temperature for 5 hours. The solution was concentrated to remove volatiles, and the residue partitioned between ethyl acetate (200 mL) and sodium bicarbonate (200 mL). The organic phase was washed with brine (200 mL), dried over sodium sulfate, and concentrated to give 4-chloro-2-(chloromethyl)-1-methylbenzene (Cpd MM, 17.5 g, 87% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.33 (d, J=2.20 Hz, 1H), 7.20-7.25 (m, 1H), 7.14 (d, J=8.07 Hz, 1H), 4.55 (s, 2H), 2.39 (s, 3H).
References:
US2015/361067,2015,A1 Location in patent:Paragraph 0519
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