ChemicalBook CAS DataBase List 4-Chloro-4'-fluorobutyrophenone

4-Chloro-4'-fluorobutyrophenone synthesis

10synthesis methods

Product Name:4-Chloro-4'-fluorobutyrophenone
CAS Number:3874-54-2
Molecular formula:C10H10ClFO
Molecular Weight:200.64

The purified alkyne (5 mmol) was treated with a solution of HNTf2 (60-200 mol %) in 1,4-dioxane in apreheated oil bath at 100°C, under magnetic stirring, for 18-52 h, and the corresponding ketone was purified by column chromatography after cooling 4-Chloro-4'-fluorobutyrophenone. The reaction crude was purified by column chromatography using 20% AcOEt in n-hexane as an eluent. Isolated yield: 850 mg (85%). R f (20% AcOEt in n-hexane): 0.66. GC-MS (m/ z, M+? 200), major peaks found: 200 (1%), 164 (1%), 138 (43%), 123 (100%), 107 (10%). 1H NMR (δ, ppm; J, Hz): 8.03-7.97 (2C-H arom, mult), 7.17-7.09 (2C-H arom, mult), 3.68 (CH2, t, J = 6.2), 3.15 (CH2, t, J = 7.0), 2.22 (CH2, tt, J = 7.0, 6.2). 13C NMR (δ, ppm; J, Hz): 197.3 (C=O), 166.1 (C, d, J 1 C-F = 254.7), 133.2 (C, d, J 4 C-F = 4.3), 130.6 (2CH, d, J 3 C-F = 9.3), 115.9 (2CH, d, J 2 C-F = 22.2), 44.6 (CH2), 35.2 (CH2), 26.7 (CH2).
4-Chloro-4'-fluorobutyrophenone synthesis

4-Chloro-4'-fluorobutyrophenone synthesis

462-06-6
414 suppliers
$10.00/5g

4635-59-0 Synthesis

4635-59-0
465 suppliers
$17.67/10gm:

3874-54-2
361 suppliers
$10.00/5G

Yield:3874-54-2 90%

Reaction Conditions:

with aluminum (III) chloride in dichloromethane at 20; for 4 h;Time;

Steps:

1-2

Mix 16 g of fluorobenzene and 20 g of dichloromethane to obtain a fluorobenzene dichloromethane solution (the temperature of the ice bath is guaranteed to be 5°C);After mixing 20g 4-chlorobutyryl chloride and 20g dichloromethane fourth,Obtain a mixed solution of 4-chlorobutyryl chloride and dichloromethane;The mixture of 4-chlorobutyryl chloride and dichloromethane was added dropwise to the fluorobenzene dichloromethane solution at a drip rate of 70 drops/min and mixed with 20 g of anhydrous aluminum chloride, and the second substitution was carried out at 20°C. Reaction for 4h; after the completion of the second substitution reaction, the product of the second substitution reaction is transferred to 600g of ice water for quenching reaction at a speed of 200r/min for 0.3h; the product after the quenching reaction is liquid-separated; The organic phase obtained from the liquid was mixed with 4g of anhydrous sodium sulfate to remove water, then filtered and concentrated (50°C),Obtain 4-chloro-1-(4-fluorophenyl)butan-1-one (with a yield of 90% and a purity of 99%);

References:

CN112538042,2021,A Location in patent:Paragraph 0089; 0095; 0098; 0104

1183278-95-6 Synthesis