SU614085A1 - Method of obtaining 4-cyano-2,3,5,6-tetrafluorodiphenyl esters - Google Patents

Description

(54) STYOOSHIFT 4-IIANO-2,3.5,6-TE1RAFTYURDIPHENYL ETHERS

The present invention relates to a method for the preparation of undeliverable difeine ethers of the general formula

T T

/

P f

where R is chlorine, nitro, acetylamino, lower alknl;

n 1 or 2.

which can be used as physiologically active substances.

A known method for the preparation of tetrafluorine-containing diphenyl ether is carried out by treating the fully fluorinated benzene with a phenol in a polar solvent (for methylformand) for 2 hours at 120 ° C | 1.

The application of the conditions of this method for obtaining diphenyl efnrov of the general formula (1) does not give the desired result because of the involvement in the reaction, besides fluorine atoms, also of an indyl group.

A method for the preparation of diphenyl ethers of the general formula (I) is proposed, in that the corresponding phenol

Caln treated with pentafluorobenzonetrile in an environment of tert-butanol prn 70-80 ° C.

The duration of the method is 20-30 minutes. The yield of the target product 80-90%. 5 Example I. 4-СЫ-2,3,5.6-4Р-4-МО2-Diphenyl ether.

A solution of 19.3 g of pentafluorobenzonitrile in 50 ml of tert-buta iol and the mixture is poured with stirring to a solution of potassium 4-nitrophenol, 0 in tert-butanol, obtained. when serially dissolved in 100 ml of this alcohol, 5D g of potassium hydroxide and 13.9 g of 4-ntrophenol. The reaction mixture is kept for 25 minutes while being transferred and the temperature is .70-80 ° C, and then poured into water. The precipitate is filtered off, dried in air and recrystallized from nz benzene. Obtain 26.4 g (85%) of the desired product, so pl. 131 ° C.

Found,%: C 50.04; H 1.29; N 9.06; F 22.98.

C, H "NiF, O

Calculated,%: C, 01; H N 8.97; f 24.34.

The aqueous solution, which has been deactivated after the separation of the target product, contains 0.0) mol of ionic fluorine, which corresponds to i / iif.io of 89 / o. -, Example city. 4-CN-2D5,6-4F-2,4-2CI-bodice: nilovy ether. A solution of 12 g of pentafluorobenzonitrile in 20 ml of tert-butanol is added at ps) meSheyvannn to potassium 2-, 4-chlorophenol prepared from 10 g of 2,4-dichlorophenol and 3.7 g of potassium hydroxide in 60 ml of tert-butanol . The reaction mass is kept for 30 minutes with stirring to ref neparype 70-SO C, and then poured into water. The desired product is extracted with ether, the ether extract is dried with calcium chloride and distilled in vacuo. Obtain 17 g (84Vo) of the desired product, BP. 167-70 ° C / / 3 1, m Hg, so pl. 32-33 ° C.

"

VA.09 a, 7S S.OO

xzo

80

86

53.63 2.ei v, 5c

leo

183 EACH FOR GEESV & c.

Nerves

Prv. 2 mm Hg. cf.

Claims (1)

Invention Formula Method for preparing 4-cyano-2,3,5,6-tetrafluoride diphenyl ethers of the general formula F f m, j ,, 59.70 2.51 4.98 27, OZ Se.S9 55.56 2.4 8.64 23.44 22.97 where R is chlorine, ntro-, acetylamino, lower alkyl; Claim 1 or 2, characterized in that. that the corresponding potassium phenol is treated with pentafluorobenzonitrile in tert-butanol medium at 70-80 ° C. Sources of information taken into account in the examination: I. Second Certificate of the USSR No. 418465, cl. C 07 C 43/20, 1971. N,%: N 4.47; F 21.59; ; 1 21 19 C.sHsNF.CUO Calculated, / o: N 4.16; F 22.61; C1 21.09. This analysis took place at 91 / o. These analyzes and the physical constants of the remaining products, obtained by the proposed method, are shown in Table. The IR spectra of all compounds contain an absorption band in the region of 2320 cm, due to the vibrations of the nitrite group Intense absorption in the region of 1400-1100 cm is characteristic of full-fluorinated, aromatic compounds.The absorption in the region of 1600-1500 cm, caused by plane vibrations of the aromatic ring, manifests itself in three bands: 1685; 1650-1628 and 1500-1525. The high-frequency mixing in this case is caused by the presence of fluorine in the molecule.