* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
P-Fluoroaniline (100 g, 1.1 eq) and isopropanol (1730 ml, 10 V) were added and heated to 40 ° C. with mechanical stirring to precipitate a large amount of a pale yellow crystalline solid gradually, Stir over time and monitor until reaction is complete. The heating was stopped, the temperature was naturally lowered to room temperature while stirring, extraction and filtration were carried out, the filter cake was washed off with cold isopropanol, and after drying, a pale yellow crystalline substance SM 2 was obtained, the mass was 238 g , The yield is 95percent, and the purity is 99percent.
93.6%
Reflux; Large scale
The p-fluoroaniline (1.11kg, 10mol) and 4-benzyloxybenzaldehyde (2.12kg, 10mol) were added to 10L of toluene and refluxed. After the reaction was completed, the solvent was evaporated and the solvent was normal. n-hexane and ethyl acetate 10:1 Crystallization gave Compound 4 (2.85 kg) in 93.6percent yield.
Reference：
[1] Patent: JP2016/147843, 2016, A, . Location in patent: Paragraph 0016
[2] Patent: CN107793339, 2018, A, . Location in patent: Paragraph 0021; 0023; 0031; 0038
[3] Pharmacy and Pharmacology Communications, 2000, vol. 6, # 1, p. 25 - 29
[4] Journal of Organic Chemistry, 2018,
2
[ 100-39-0 ]
[ 123-08-0 ]
[ 371-40-4 ]
[ 70627-52-0 ]
Yield
Reaction Conditions
Operation in experiment
92%
Stage #1: at 20℃; for 12 h; Stage #2: for 4 h; Reflux
100 ml of DMF, p-hydroxybenzaldehyde (12.2 g, 0.1 mol), potassium carbonate (16.6 g, 0.12 mol) were successively added to a 250 ml three-necked flask, Benzyl bromide (20.4 g, 0.12 mol) was added dropwise, Room temperature reaction for 12 hours, The reaction solution was poured into ice water, Solid precipitation,filter, Washed cake, The filter cake is dry. To give benzyl-protected p-hydroxybenzaldehyde (26.2 g)Yield 91percent. And then take another 250ml single neck round bottom flask, Followed by adding 100 ml of acetone, benzyl-protected p-hydroxybenzaldehyde (14.4 g, 0.05 mol), p-fluoroaniline (5.55 g, 0.05 mol) After the reaction was refluxed for 4 h, the reaction solution was cooled to 5 ° C to precipitate a solid, filter, The solid was washed with cold acetone, The solid was dried to give N-(4-fluorophenyl)-4-benzyloxybenzylideneamine (Compound IV) 14g, Yield 92percent.
Reference：
[1] Patent: CN106397292, 2017, A, . Location in patent: Paragraph 0092; 0093
[2] Patent: WO2008/96372, 2008, A2, . Location in patent: Page/Page column 17
3
[ 3382-63-6 ]
[ 100-44-7 ]
[ 70627-52-0 ]
Yield
Reaction Conditions
Operation in experiment
20.3 g
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2 h;
The formula EZ-2 is a structural formula of 4-[[(4-fluorophenyl)imino]methyl]-phenol.4-[[(4-Fluorophenyl)imino]methyl]-phenol (21.5 g, 0.1 mol) was dissolved in 20 ml of DMF.Potassium carbonate (27.6 g, 0.2 mol) was added in sequenceChlorobenzyl (12.6 g, 0.1 mol),After the addition, the mixture was stirred at room temperature for 2 h.TLC judged the end of the reaction, poured the reaction solution into ice water, and filtered by suction.The filter cake was dried in vacuo to give a white solid (20.3 g).
Reference：
[1] Patent: CN109369491, 2019, A, . Location in patent: Paragraph 0036-0039; 0060-0062
4
[ 123-08-0 ]
[ 70627-52-0 ]
Reference：
[1] Patent: JP2016/147843, 2016, A,
5
[ 100-44-7 ]
[ 70627-52-0 ]
Reference：
[1] Patent: JP2016/147843, 2016, A,
6
[ 99395-88-7 ]
[ 70627-52-0 ]
Reference：
[1] Patent: CN105439929, 2016, A, . Location in patent: Paragraph 0029
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