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[ CAS No. 88675-31-4 ]

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CAS No. :88675-31-4 MDL No. :MFCD00699290
Formula : C14H10BrFO Boiling Point : 356.4±27.0°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :293.13 g/mol Pubchem ID :11300837
Synonyms :

Safety of [ 88675-31-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 88675-31-4 ]

  • Upstream synthesis route of [ 88675-31-4 ]
  • Downstream synthetic route of [ 88675-31-4 ]

[ 88675-31-4 ] Synthesis Path-Upstream   1~4

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YieldReaction ConditionsOperation in experiment
94.8% With hydrogen bromide; bromine; acetic acid In dichloromethane at 26℃; EXAMPLE-2; 2-Bromo- 1 -(4-fluorophenyl)-2-phenylethanone; Methylene chloride (1L) is taken in a 4 necked RB flask equipped with mechanical strring rod, pressure equalization funnel and a CaCl2 guard tube. 100 g (0.466 mol) of l-(4-Fluorophenyl)-2-phenyl ethanone is introduced in to the above flask and stirred for 5 minutes to obtain a clear solution.2ml of a 30percent hydrobromic acid in acetic acid is then added , followed by gradual addition of a cold solution of bromine (73 g, 0.456 mole) in 200ml of methylene chloride at 26+/-2°C. Bromine solution is added in such a manner that it is consumed instantly as indicated by colouration of reaction mixture. After addition of bromine solution the reaction mixture is cooled to 19+/-1°C , treated with 5percent aqueous sodium sulphite ( 200 ml) and stirred for about lhr at 21.5+/-3.5°C. The organic layer is then separated and is subjected to the above operation twice with 5percent aqueous sodium sulphite (2 x 200ml).The organic layer is then stirred with 5percent aqueous sodium bicarbonate (200 ml) for about 1 hr at 21.5+/-3.5 C and separated.. The organic layer is finally stirred with 5percent aqueous sodium chloride(200ml) and separated. The organic layer is dried over sodium sulphate and filtered. Methylene chloride is removed by distillation and the syrup thus obtained solidified on standing in to a pale orange coloured solid. Yield 129 g ( 94.8percent)
92% With copper(II) nitrate trihydrate; hydrogen bromide; oxygen In acetic acid at 60℃; for 4.5 h; Green chemistry The representative example of oxidative bromination is described as follows: A mixture of 1.2 g acetophenone 1a (10 mmol) and 0.121 g Cu(NO3)2•3H2O (0.5mmol) was stirred and an oxygen balloon (about 0.5–1 L) was attached to the reaction system. Then 8mol/L aqueous solution of hydrobromic acid (1.5mL, 12mmol) was added dropwise to the mixture. The reaction mixture was then stirred at 70°C and monitored by TLC or GC. After the completion of the reaction, the mixture was extracted with CH2Cl2. The organic extract was first washed with 5percent sodium sulfite, saturated sodium bicarbonate solution, and then water and finally dried over anhydrous magnesium sulfate. The solvent was removed under vacuum and the residue was purified by column chromatography (silica gel, petroleum ether/dichloromethane 3:1) to afford the product, α-bromoacetophenone (2a) in 1.81 g, yield: 91percent.
90% at 40℃; for 16 h; The third step, 10.7g 4-fluorophenylacetophenone was dissolved in 100ml of glacial acetic acid, 40percent hydrobromic acid was added 15ml, stirred,Slowly dropping 30percent mass fraction of hydrogen peroxide 9ml, 40 reaction 16h, TLC trace showed the end of the reaction.Unreacted bromine was removed by adding saturated aqueous sodium sulfite to the reaction mixture.The reaction mixture was extracted with 200 ml of ethyl acetate and an appropriate amount of aqueous sodium carbonate. The organic layer was separated and the organic layer was washed twice with aqueous sodium carbonate solution and dried over anhydrous magnesium sulfate.After filtration and spin drying, 13.25 g of 2-bromo-1- (4-fluorophenyl) -acetophenone was obtained as a yellow thick liquid in a yield of 90percent.
88% With copper(ll) bromide In dichloromethane; ethyl acetate for 18 h; Reflux; Inert atmosphere General procedure: Copper(II) bromide (CuBr2, 268 mg, 1.2 mmol) was added to a solution of skeleton 5 (1.0 mmol) in the co-solvent of EtOAc and CH2Cl2 (1:1, 20 mL), at 25 °C. The reaction mixture was stirred at reflux for 18 h. The reaction mixture was cooled to 25 °C. Saturated NaHCO3 (5 mL) was added to the reaction mixture and the solvent was concentrated. The residue was diluted with water (10 mL) and the mixture was extracted with EtOAc (3 x 20 mL). The combined organic layers were washed with brine, dried, filtered and evaporated to afford crude product. Purification on silica gel (hexanes/EtOAc = 10/1-6/1) afforded skeletons 3 and 6.
85%
Stage #1: With hydrogen bromide In water at 20℃; for 0.0833333 h; Darkness
Stage #2: With bromine In water at 20℃; for 5 h;
Stage #3: With dihydrogen peroxide In water at 20℃; for 12 h;
Compound 4 (5.00 g, 23.34 mmol) was suspended in water (15 mL) in a flaskcovered with aluminum foil. Five drops of 40 percent aqueous solution of HBr was added.The mixture was stirred at room temperature for 5 min, Br2 (2.05 g, 12.84 mmol) wasadded dropwise. The reaction mixture was stirred at room temperature for 5 h, and30 percent aqueous solution of H2O2 (6.5 mL, 25.70 mmol) was slowly added. After 12 h,dichloromethane (30 mL) was added and the organic layer was washed with 5 percentaqueous sodium sulfite (10 mL) and 5 percent aqueous sodium chloride (2×20 mL) andthen dried over anhydrous magnesium sulfate. The organic mixture was concentrated to give a light yellow oil 5 (5.82 g, 85 percent yield). 1H NMR (600 MHz, CDCl3) δ: 8.01–7.98 (m,2H), 7.49 (d, J=7.2 Hz,2H), 7.36–7.30 (m,3H), 7.07 (t, J=8.6 Hz,2H), 6.32 (s,1H). 13C NMR (150 MHz, CDCl3) δ: 189.33, 166.29, 164.59,135.52, 131.69, 131.63, 130.04, 128.89, 128.74, 115.71, 115.57, 51.07.

Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6479 - 6494
[2] Patent: WO2012/143933, 2012, A1, . Location in patent: Page/Page column 13-14
[3] Synthetic Communications, 2016, vol. 46, # 2, p. 165 - 168
[4] Patent: CN106397296, 2017, A, . Location in patent: Paragraph 0018; 0021; 0024; 0027; 0030; 0033; 0036; 0039
[5] Tetrahedron, 2017, vol. 73, # 34, p. 5207 - 5213
[6] Synthetic Communications, 2015, vol. 45, # 24, p. 2832 - 2840
[7] Tetrahedron, 1969, vol. 25, p. 969 - 984
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Reference: [1] Patent: WO2012/143933, 2012, A1,
[2] Synthetic Communications, 2015, vol. 45, # 24, p. 2832 - 2840
[3] Patent: CN106397296, 2017, A,
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  • [ 88675-31-4 ]
Reference: [1] Patent: WO2012/143933, 2012, A1,
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Reference: [1] Patent: CN106397296, 2017, A,
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