4-Bromo-2,5-dimethylphenol

General procedure: To a magnetic solution of aromatic compound (1 mmol)in acetonitrile (5 mL), OXBTEATB (0.233 g, 0.5 mmol) wasadded and stirred at room temperature for the appropriatetime (Table 1). The reaction was monitored by TLC (eluent:n-hexane/ethyl acetate: 5/1). The reaction mixture was transferredinto a separatory funnel after filtration of OXBTEABand was extracted with water (15 mL) and dichloromethane(20 mL). The organic layer was dried over anhydrousNa2SO4, and the solvent was concentrated in a rotary evaporator.The crude product was purified by passing it over acolumn of silica gel using a mixture of n-hexane and ethylacetate as the eluent. In order to regenerate the reagent, whitesolid was treated with liquid bromine. All the product structureswere confirmed by comparison of melting point or 1HNMR spectra with ones reported in the literature [29a-29e].To a stirred suspension of 2, 5-dimethyl phenol (5.0 g, 40.9 mmol) in H20 (150 mL), at room temperature was added tetrabutylammonium tribromide (19.9 g, 41. 39 mmol) in CHC13 (150 mL). The reaction mixture was stirred for 2 h at rt, the organic layer was separated and dried over Na2S04, filtered and concentrated. The residue was purified by column chromatography on silica gel eluting with hexane-ethyl acetate (1: 5) to afford 2, 5-dimethyl-4-bromophenol as a brown solid (6.2 g, 76percent) ; 1H NMR (300 MHz, DMSO-d6) :8 9.47 (s, 1 H), 7.24 (s, 1 H), 6.74 (s, 1 H), 2.21 (s, 3 H), 2.07 (s, 3 H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase = hexanes-ethyl acetate (9: 1) ; Rf = 0. 52.To a stirred suspension of 2, 5-dimethyl phenol (5.0 g, 40.9 mmol) in HTo a stirred suspension of 2, 5-dimethyl phenol (5.0 g, 40.9 mmol) in H20 (150 mL), at room temperature was added tetrabutylammonium tribromide (19.9 g, 41. 39 mmol) in CHC13 (150 mL). The reaction mixture was stirred for 2 h at rt, the organic layer was separated and dried over Na2S04, filtered and concentrated. The residue was purified by column chromatography on silica gel eluting with hexane-ethyl acetate (1: 5) to afford 2, 5-dimethyl-4-bromophenol as a brown solid (6.2 g, 76percent) ; 1H NMR (300 MHz, DMSO-d6) :8 9.47 (s, 1 H), 7.24 (s, 1 H), 6.74 (s, 1 H), 2.21 (s, 3 H), 2.07 (s, 3 H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase = hexanes-ethyl acetate (9: 1) ; Rf = 0. 52.

Molecular Weight:201.06
XLogP3:3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:199.98368
Monoisotopic Mass:199.98368
Topological Polar Surface Area:20.2
Heavy Atom Count:10
Complexity:116
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes