2-Bromo-1-(2-fluorophenyl)ethanone

Liquid

Reference Example 33 To a solution of 1-(2-fluorophenyl)ethanone (15.1 g) in acetic acid (150 mL) was added bromine (5.8 mL). The mixture was stirred at room temperature for 2 hr, and concentrated under reduced pressure. A saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound as a pale-yellow oil (yield 22.9 g, yield 97percent). General procedure: Oxone (1.352 g, 2.2 mmol) was added to the well stirred solution of substrate (2 mmol) and NH250 kg of o-fluoroacetophenone and 500 liters of methyl tert-butyl ether were added to a 1000-liter reactor. Open the salt water system, stir to cool to 0 ° C, add 2.5kg of aluminum chloride, about 15min, after adding NBS 375kg (25kg each time to join), temperature control does not exceed 5 ° C. Plus finished, naturally warming to room temperature.After the reaction for 4 h, the dosing plate was monitored for no raw material, and the resulting solution was concentrated under reduced pressure to 50percent. A large amount of water was added to the substrate, the by-product was washed, the oil layer (lower layer), anhydrous Na2S04 Dry, filtered, filtrate under reduced pressure distillation, collecting 82 ~ 84 ° C (5mmHg) fractions, calculated yield of 80percent, 5percent higher than the small testGeneral 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, 510mmol 2-fluoroacetophenone is added to a 100mL round bottom flaskAnd 11mmol of N-bromosuccinimide (NBS), 35mL of ethyl acetate dissolved, Then 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/dichloromethane) gave white crystals in 24percent yield.General 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.

A new class of acetophenone-based cinchona alkaloid-derived quaternary ammonium salts were prepared and evaluated as phase-transfer catalysts in the enantioselective alkylation of glycine imine ester.

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:149
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes