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ChemicalBook CAS DataBase List 3-chloro-5-hydroxy-benzonitrile
473923-97-6

3-chloro-5-hydroxy-benzonitrile synthesis

4synthesis methods
473923-96-5 Synthesis
3-chloro-5-methoxybenzonitrile

473923-96-5
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Yield:473923-97-6 94%

Reaction Conditions:

Stage #1:3-chloro-5-methoxybenzonitrile with lithium iodide in 2,4,6-trimethyl-pyridine at 170; for 4 h;
Stage #2: with hydrogenchloride in 2,4,6-trimethyl-pyridine;water at 20;

Steps:

3.2; 3.3
A 250 mL flask was charged with 24b (7.0 g, 41.766 mmol) and 2,4,6-collidine (100 mL). The mixture was heated to 170° C. and Lil (16.76 g, 125.298 mmol) was added and the reaction mixture was heated for 4 h. When 24b was consumed the reaction was cooled to RT and quenched with 10% aqueous HCl. The resulting mixture was extracted with EtOAc and washed with water and brine. The EtOAc extract was dried(Na2SO4) and filtered. The solvent was removed in vacuo to afford a yellow oil which was purified by silica gel chromatography eluting with EtOAc/hexane (10:90) to afford 6.0 g (94%) of 24c.

References:

Roche Palo Alto LLC US2007/88015, 2007, A1 Location in patent:Page/Page column 22

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1213790-87-4 Synthesis
3-Chloro-5-[(4-Methoxybenzyl)oxy]benzonitrile

1213790-87-4
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