2-Bromo-4-methylphenol

clear colourless to pale yellow liquid

General procedure: To a 10 mL round bottom flask equipped with a magnetic stir bar were added phenols or alkenes (0.1 mmol), CBrGeneral procedure: To a 10 mL round bottom flask equipped with a magnetic stir bar were added phenols or alkenes (0.1 mmol), CBrGeneral procedure: Reaction conditions: Thiourea (5.1 molpercent, 2 mg, 0.026 mmol) was added to an acetonitrile solution (10 mL) containing NBS (1.15 equiv, 104.4 mg, 0.587 mmol). Anisole (56.3 mg, 0.51 mmol) was added immediately to the resulting stirred solution and allowed to stir at room temperature for 10 min. The reaction was quenched by the addition of 10percent aqueous solution of NaGeneral procedure: To a solution of 4-alkylphenol (20 mmol) in chloroform (20 mL), sodium hydrogencarbonate (2 g, 24 mmol) was added. The resulting suspension was cooled to 0°C. While a solution of elementary bromine (1.12 mL, 22 mmol) in chloroform (8 mL) was slowly added, the suspension was vigorously stirred. After completion of the reaction, monitored by TLC the suspension was filtered. The filter with the solid residue was rinsed once with 50 mL of chloroform. The combined organic solutions were evaporated under reduced pressure. The final workup of the product was done either by distillation or by column chromatography (petroleum ether : ethyl acetate, 9 : 1).General procedure: Phenol (1 mmol, 10 mL) dissolved in 1M PEG-600, isoquinolinium dichromate (IQDC) or isoquinolinium chlorochromate (IQCC) reagent, and tetrabutylammonium halide (TBAX) (1.1 mmol each) were taken in a reaction flask and refluxed with constant stirring at about 25 to 30 C, till the completion of reaction, as as certainedby thin layer chromatography. Then the contents of reaction were diluted with ethyl acetate (10 mL) and separated from aqueous layer. Organic layer was then washed two to three time swith 5 mL water and separated. Finally, the resultant mass is dried over sodium sulphate. The anhydrous ethyl acetate layerwas separated under reduced pressure to give crude product, which was further purified by column chromatography (silicagel, 100-200 mesh) using EtOAc-hexane (3:7). For the separation and recyclization of PEG, aqueous mother liquor (reaction mixture of PEG-600 and water) was treated with ether because PEG is insoluble in ether. The aqueous layer obtained after the removal of ether, was then distilled directly at 100 C to remove water and recover PEG-600. The recovered PEG-600 could be reused for consecutive runs.General procedure: A centimolar (0.01mol) organic substrate (phenols, anilines, or acetanilides), about 0.01 mol of potassium halide (KBr orKI), 0.001 mol hypervalent Cr (VI) reagent (IQCC orIQDC), and solvent (DCE or ACN) were taken in a previouslycleaned round-bottom flask. About 50 mg of KHSO4 isalso added to the reaction flask. The reaction mixture isrefluxed for about 4–5 h at 50–60C. Progress of the reactionwas monitored by TLC technique. After completion, thereaction mixture is treated with 5percent sodium thiosulfate solutionfollowed by the addition of ether. The aqueous layer wasseparated, dried, and evaporated under vacuum, and purifiedwith column chromatography using chloroform:n-hexane(9:1) as eluent to get pure productGeneral procedure: NHA solution of the starting material (~10 mmol) and pTsOH (10 mol percent) in MeOH (1.0 mL per mmol starting material) was stirred for 10 min, then a solution of NBS (100 mol percent; recrystallized from HGeneral procedure: Complex 2a (6 mg, 0.015 mmol) and p-cresol (198 mg, 1.8 mmol) were dissolved in CH3CN (10 mL). To this mixture, KBr (440mg, 3.7 mmol)dissolved in water (2 mL) was added, followed by 30percent H2O2 (1 mL) added dropwise with constant stirring. The pH of the solution wasadjusted to approximately 3 by dropwise addition of 2N HCl solution.The reaction mixture was stirred for 20 h at room temperature. Theproduct was extracted with diethyl ether and concentrated to about1 mL. Two products, 2-bromo-4-methylphenol and 2, 6-dibromo-4-methylphenol, were separated by TLC and characterised byspectroscopic techniques. The isolated yields were 79 mg and 60 mg, respectively. The results of the conversions are given in Table 3. Thesame reaction was carried out keeping all other components andconditions the same but not adding the catalyst.General procedure: Reaction conditions: Thiourea (5.1 molpercent, 2 mg, 0.026 mmol) was added to an acetonitrile solution (10 mL) containing NBS (1.15 equiv, 104.4 mg, 0.587 mmol). Anisole (56.3 mg, 0.51 mmol) was added immediately to the resulting stirred solution and allowed to stir at room temperature for 10 min. The reaction was quenched by the addition of 10percent aqueous solution of Na

Molecular Weight:187.03
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:185.96803
Monoisotopic Mass:185.96803
Topological Polar Surface Area:20.2
Heavy Atom Count:9
Complexity:94.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes