4-Fluorophenacyl bromide

beige to light grey-green cryst. powder or flakes

General procedure: Oxone (1.352 g, 2.2 mmol) was added to the well stirred solution of substrate (2 mmol) and NH25 g of compound 1 (p-fluoroacetophenone) (0.18 mol) was dissolved in 50 mL of cyclohexane, and 2-3 drops of bromine were added dropwise, and the temperature was raised to 40 ° C.After the color of bromine was found to fade, the temperature was lowered to 0 ° C.29 g of liquid bromine (0.18 mol) was added dropwise, and the reaction was carried out for 0.5 hour.When GC was detected without Compound 1, it was washed successively with saturated aqueous sodium carbonate solution, 5percent by mass of sodium chloride solution and water.Dispensing, drying, The toluene was distilled off under reduced pressure to give 39 g of Compound 2, The purity was 95.0percent, and the yield was 94.8percent.General procedure: N-bromosuccinimide (0.37 mmol) was added to the stirredsolution of acetophenone (2) (0.37 mol, 1 equiv) in acetonitrile(40 mL). The resulting reaction mixture was stirredfor 10–15 min. After that p-TsOH (0.74 mmol, 2 equiv) wasadded to the reaction mixture and refluxed for 4–5 h andmonitored by TLC. After completion of reaction, reactioncontent was brought to room temperature and washed withsaturated solution of sodium bicarbonate and extracted withethyl acetate (3 × 20 mL), organic layer was dried oversodium sulphate and concentrated under reduced pressure.The obtained residues were purified by column chromatographyusing silica 100–200 mesh size by ethyl acetate:hexane (4:96) mixture and pure compound was identified as2-bromo-1-phenyl-ethanone 3a–g.10 g (72.4 mmol) of p-fluoroacetophenone was dissolved in 100 mL of acetonitrile, and 11.57 g (72.4 mmol)Br2 in acetonitrile, stirred overnight (8-10h). After the reaction was complete, the solvent was removed by steam under reduced pressure, the ethyl acetate was re-dissolved, washed with brineWashed three times, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by steaming under reduced pressure. The solvent was filtered through 50 mL of cyclohexane and a few drops of ether to obtainTo 14.2 g of white crystals, yield: 90.8percent.20 g (144.7 mmol) of p-fluoroacetophenone was dissolved in 200 mL of acetonitrile, and 23.12 g (144.7 mmol)Br2 in 50 mL of acetonitrile was stirred at room temperature overnight. After completion of the reaction, the reaction solution was concentrated and concentrated with ethyl acetateWashed with brine three times, dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off under reduced pressure. The resulting white oil was evaporated at low temperatureCuring, with 100mL n-hexane plus 1mL ethyl acetate beating, filter white solid 28g, the yield: 89.2percent, 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(NOGeneral procedure: Acetophenone (0.55 mmol) and 100 mL glacial acetic acid taken in beaker. Similarly, bromine (0.125 mmol) and 100 mL glacial acetic acid taken in another beaker and it added drop by drop in the solution of acetophenone and glacial acetic acid with occasionally shaking. Reaction mixture was transferred in an Erlenmeyer flask and irradiated under microwave irradiation for 15 min with a time interval of 35 s, after the completion of reaction indicated by TLC, poured in ice water, isolated the solid and recrystallized from ethanol (Scheme-I). Physico-chemical data of the synthesized compounds are given in Table-1.General procedure: In a RBF cooled in ice bath at 0 C, HBr(12 mmol, in 2 ml of water) was taken. To this a solution of NaNOPreparation 10 mmol 4-fluoroacetophenone is added to a 100 mL round bottom flaskAnd 11mmol of N-bromosuccinimide (NBS), Dissolve 35mL of ethyl acetate and add 1g of Amberlyst 15 ion exchange resin as catalyst.The reaction was warmed to 40°C and reacted. After TLC tracks the reaction, The reaction solution was filtered to remove Amberlyst 15 ion exchange resin, and the filtrate was spin-dried.Column chromatography (eluent: petroleum ether/ethyl acetate) gave green crystals in 73percent yield.General procedure: A modified reaction route: NBS (1.2 equiv.) was added to a solution of appropriately substitutedacetophenones 9a–9l (1.0 equiv.) in CH3CN (15 mL) with p-TSA (0.2 equiv.). The solution washeated at 80 °C for 3-5 h until all the starting materials had been consumed (TLC monitored). Thereaction mass was poured in ice-cold water and extracted with DCM (3 × 20 mL). Anhydrous Na2SO4was added to the combined organic layer, filtered and the excess solvent was removed under reducedpressure. The resultant solid/ liquid obtained were washed with hexane to yield compounds 10a–10i.4, 5 2-Bromo-1-(4-fluorophenyl)ethan-1-one (10a): Light brown solid, yield 69percent. M. p. 47-49 (°C).1-(4-Fluorophenyl)ethanone (9.00 g, 65.15 mmol, 1.00 eq) was dissolved in acetic acid (100.00 mL), liquid bromine (10.41 g, 65.15 mmol, 1.00 eq) was added at 15 °C and the mixture was stirred for 20 minutes. Step 1 : Synthesis of 2-bromo-l -(4-fluorophenyl) ethan-l-one: [0234] To the stirred solution of 4-Fluoroacetophenone (10 g, 71.9 mmol) in 200 mL of MeOH at 0°C was added Bromine (3.7 mL, 23.1 mmol) (dropwise addition) and stirred for about 30 minutes and stirred for about 2 hours at room temperature. After completion of the reaction (monitored by TLC), the reaction mixture was concentrated and the crude product was dissolved in n-hexane and stirred for about 30 minutes. The obtained solid was filtered and washed with n-hexane then dried and proceeded for next step (wt: 14.0 g).General procedure: A mixture of haloalkyne (0.2 mmol), tetrafluoroboric acid (20 molpercent, 40percent  aqueous solution ) in 2, 2, 2-trifluoroethanol (1 mL) was stirred at 80°C for 2 or 10 h. After the reaction was finished, water (5 mL) was added and the solution was extracted with ethyl acetate (3×5 mL), the combined extract was dried with anhydrous MgSOGeneral procedure: A mixture of haloalkyne (0.5 mmol), AgF (5molpercent) and water (1 equiv.) in TFA (1 mL) was stirred at 40°C for 6h, after which TFA was distilled out for reuse. The residue was separated by column chromatography to give the pure sample.General procedure: The reaction mixture of In(OTf)General procedure: To a solution of olefin (1mmol) in acetone (3mL) and water (0.1mL), TsNBrGeneral procedure: To a stirred solution of alkyne (1 mmol) in ethyl acetate(1 mL), 0.1 mL of acetone:water (1:1) and TsNBr2 (2 mmol) wasadded. After 10 min Na2SO3 (8 mmol) was added and the reaction was stirred at room temperature till completion asmonitored by TLC. The organic layer was extracted with ethylacetate, washed with water, dried with Na2SO4 and concentrated.The crude product was purified by flash chromatographyon silica gel (230-400 mesh) using petroleum ethereethyl acetateas eluent.

2-Bromo-4’fluoroacetophenone is a intermediate in the synthetic preparation of competitive inhibitors of aromatase.

Molecular Weight:217.03
XLogP3:2.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:215.95861
Monoisotopic Mass:215.95861
Topological Polar Surface Area:17.1
Heavy Atom Count:11
Complexity:141
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes