2-Bromo-1-(2-hydroxyphenyl)ethanone

Off-White Powder

General procedure: In a 50mL round bottom flask equipped with a magnetic stirringbar, 2-hydroxyacetophenone (10 mmol) were added. To this solution, KBr (40 mmol) dissolved in 20 mL water was added and thendissolved by stirring at ambient temperature followed by additionof a 30percent H2O2 (4 mmol). To this reaction mixture, vanadium(V)complex (0.01 mmol) and 70percent HClO4 (4 mmol) were added and thereaction mixture was stirred at 0 C and then after 10 min at roomtemperature. An additional 4 mmol of 70percent HClO4was further addedin three equal portions after every 10 min with continuous stirring.In addition, all the reactions were monitored using thin layerchromatography. The NMR spectra of bromination products aregiven in the supporting information.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, 5General procedure: The viscous liquid which is obtained from step s1.2 was hydrolysed by the suitable hydrochloric acid in aqueous media for 4 h under reflux condenser. The reaction mixture was poured into ice-water. The crystalline raw product was filtered, washed with water and three times recrystallized from ethanol.General procedure: A solution of bromine (0.27 mL, 5 mmol) inacetic acid (10 mL) is added stepwise to a solution of DHA 1 (0.84 g, 5 mmol) in acetic acid (20 mL). After a reflux of 2h, the reaction mixture was poured into water (100 mL) and ice (50 g). The obtained solid was filtered-off andrecrystallized from a 1:1 mixture of hexane-chloroform, being compound 2c obtained as yellow crystals (0.75 g, 61percent):mp 117°C (mp 118-119 ).

Molecular Weight:215.04
XLogP3:2.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:213.96294
Monoisotopic Mass:213.96294
Topological Polar Surface Area:37.3
Heavy Atom Count:11
Complexity:147
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes