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ChemicalBook CAS DataBase List 4,5-DICHLOROPHTHALONITRILE
139152-08-2

4,5-DICHLOROPHTHALONITRILE synthesis

4synthesis methods
-

Yield:139152-08-2 86%

Reaction Conditions:

with trichlorophosphate in pyridine;methanol;water

Steps:

1.iv ii)
iv) 4,5-Dichlorophthalonitrile A solution of the 4,5-dichlorophthalamide (182.6g, 0.78mol) in pyridine (1.3 litres) was cooled to 0°C and phosphorus oxychloride (187cm3) was added dropwise over 1 hour maintaining the temperature below 0°C. The mixture was allowed to warm to room temperature and left to stand for 48 hours during which time a brown purple colour developed. The mixture was poured into ice/water (5 litres) and the solid was collected by filtration and washed with ice/water (1.5 litres) and cold methanol (500ml) and then dried in vacuo at 80°C to leave a brown solid. The solid was recrystallized from acetone and water to yield the desired 4,5-dichlorophthalonitrile (120.5g, 86%) as a beige solid, m.p. 178-181°C; ν max (KBr) 2238 (CN) cmmin1; Found: %C 49.1, %H 1.2, %N 14.3. C8H2N2Cl2 requires %C 48.7, %H 1.0, %N 14.2.

References:

ZENECA LIMITED EP638614, 1995, A1

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