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Diphenylalkyl halide or diphenyl carboxylic acid and synthesis method thereof

A technology of diphenyl alkyl halide and diphenyl carboxylic acid, which is applied in the field of simple synthesis, and can solve the problems of high price, troublesome synthesis, poor repeatability, etc.

Active Publication Date: 2013-09-25
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The above-mentioned method has the following deficiencies, the substituted benzophenone in the method one, the raw materials such as bromocyclopropane and magnesium bromide are more expensive or the synthesis is more troublesome; the bromocyclopropane format reaction operation requires high requirements and poor repeatability

Method used

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  • Diphenylalkyl halide or diphenyl carboxylic acid and synthesis method thereof
  • Diphenylalkyl halide or diphenyl carboxylic acid and synthesis method thereof
  • Diphenylalkyl halide or diphenyl carboxylic acid and synthesis method thereof

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Embodiment 1

[0045] Embodiment 1: the preparation of substituted 4,4-diphenylbutyl bromide (4)

[0046]

[0047] General experiment operation:

[0048] A dry 250mL three-necked flask was connected with a reflux condenser, and magnesium chips (2.32g, 97mmol) and several grains of iodine were added, the vacuum was changed three times, and 20mL of dry THF was added. The bromobenzene derivative (100 mmol) and 20 mL of dry THF were added to the dropping funnel, and a quarter of the mixture was first added to initiate the Grignard reaction (heating if necessary). After the iodine color disappears, continue to react for half an hour and slowly add the remaining mixture. After the magnesium flakes disappeared, continue to react for half an hour and then slowly drop in 1,4-butyrolactone (3.44g, 40mmol) and 20mL of dry THF, a little exotherm. After dripping, heat to reflux for about 3 hours, stop the reaction, quench with 1M hydrochloric acid, extract three times with ethyl acetate, wash the or...

Embodiment 24

[0079] Embodiment 24, the preparation of 4-diphenyl 1-butyric acid compound (6)

[0080]

[0081] Add 262mg (1mmol) into a 100mL three-necked flask, add 10ml of acetone, cool to zero, add dropwise the pre-configured Jones reagent, a precipitate is formed, the color of the solution changes from green to orange red, and after the color remains unchanged for half an hour, add isopropyl Alcohol, the solution turns green again. After the solid was filtered out with suction, spin-dried, extracted with ether, washed with saturated sodium bicarbonate and sodium chloride, and dried over anhydrous sodium sulfate. Spin-dried and passed through the column to obtain 285 mg (>99%) of oily substance.

[0082] 4,4-bis(4-fluorophenyl)butanoic acid (6)

[0083] 1 H NMR (300MHz, CDCl 3 )δ7.13-7.18 (m, 4H), 694-7.00 (m, 4H), 3.92 (t, J=6.0Hz, 1H), 2.30-2.33 (m, 2H); LREI-MS m / z: 376 [M] + , 258, 229, 216, 203, 183, 125, 109, 75, 57, 43.

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Abstract

The invention relates to diphenylalkyl halide or diphenyl carboxylic acid and a simple and convenient synthesis method thereof. The method comprises the following steps of: after a bromobenzene derivative and magnesium form a Grignard reagent, reacting the Grignard reagent and lactone, and opening loop to obtain 1,1-diphenyl-diol; reacting the 1,1-diphenyl-diol under the condition of a mixed solvent of an organic solvent and an acid to form diphenylenol; reacting the diphenylenol, a halogen or a halide and triphenylphosphine in the organic solvent to form diphenylalkenyl halogen; and reacting the diphenylalkenyl halogen and hydrogen to form diphenylalkyl halide, or reacting the diphenylenol and hydrogen to form diphenyl alcohol; and reacting the diphenyl alcohol and CrO3 under the action of the organic solvent and the acid to form diphenyl carboxylic acid. The reaction raw materials are cheap; the reaction conditions are mild; and substitutional diphenylalkyl halide or diphenyl carboxylic acid compounds with different benzene rings can be synthesized.

Description

technical field [0001] The present invention relates to a class of organic compounds diphenylalkyl halides or diphenylcarboxylic acids, and their convenient synthesis methods. Background technique [0002] 4,4-Diphenylbutyl halide derivatives are an important class of pharmaceutical intermediates, which can be used as diphenylbutylamine compounds (DPBPs) (such as Fluspirilene, Penfluridol, The synthetic precursor of pimozide (Pimozide), its structural formula is as follows: [0003] [0004] The synthesis method of the target compound was searched by SciFinder system and other literature retrieval systems, and the following relevant literature reports were found. [0005] (1) Grignard reaction between substituted benzophenone and bromocyclopropane, followed by ring opening with magnesium bromide, and finally hydrogenation to obtain the target product. [Hulshof, J.W. et al. Bioorg. Med. Chem. 2006, 14, 7213.] [0006] [0007] (2) After the substituted benzophenone i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C22/08C07C43/225C07C22/04C07C57/58C07C59/64C07C57/38C07C25/18C07C17/354C07C41/20C07C51/16
Inventor 陈刚马大为袁钧瑛袁承业
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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