3-Methoxy-4-nitrophenol

To a solution of 4-fluoro-2-methoxy-1-nitrobenzene (Combi-blocks, 3.4 g, 19.9 mmol) in DMSO (40 mL) was added an aqueous solution (1N) of NaOH (40 mL, 40 mmol).Step a: To a solution of 4-fluoro-2-methoxy-1-nitrobenzene (Combi-blocks, 3.4 g, 19.9 mmol) in DMSO (40 mL) was added an aqueous solution (1 N) of NaOH (40 mL, 40 mmol). The reaction mixture was heated at 80° C. for 20 h. The mixture was cooled to room temperature, and the 'pH' of the solution was adjusted to 5 by aqueous HCl solution. The mixture was extracted with ethyl acetate three times. The combined organic extract was washed with water, brine, dried over MgSOStep a:To a solution of 4-fluoro-2-methoxy-1-nitrobenzene (Combi-blocks) (3.4 g, 19.9 mmol) in DMSO (40 mL) was added an aqueous solution (1N) of NaOH (40 mL, 40 mmol). The reaction mixture was heated at 80° C. for 20 h. The mixture was cooled to room temperature, and the 'pH' of the solution was adjusted to 5 by aqueous HCl solution. The mixture was extracted with ethyl acetate three times. The combined organic extract was washed with water, brine, dried over MgSOStep 1. To a solution of 4-fluoro-2-methoxy-1-nitrobenzene (Combi-blocks, 3.4 g, 19.9mmol) in DMSO (40 mL) was added an aqueous solution (1 N) of NaOH (40 mL, 40mmol). The reaction mixture was heated at 80 oC for 20 h. The mixture was cooled toroom temperature, and the “pH” of the solution was adjusted to 5 by aqueous HClsolution. The mixture was extracted with ethyl acetate three times. The combinedorganic extract was washed with water, brine, dried over MgSO4, and concentrated togive 3-methoxy-4-nitrophenol as a light yellow solid (3.2 g, 95percent).A solution of sodium hydroxide (39 mL, 117 mmol, 3M)Was added to a solution of 4-fluoro-2-methoxy-1-nitrobenzene (10.0 g, 58.4 mmol)Of thionyl chloride(100 mL)Followed by reaction at 80 ° C for 20 hours in an oil bath.After the reaction, pH = 5 was adjusted with concentrated hydrochloric acid, Then extracted with ethyl acetate (100 mL x 3)The organic phases were combined, concentrated under reduced pressure, The residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10: 1) to give the title compound (9.0 g, yield 90.1percent).(0915) 2-Methoxy-4-fluoronitrobenzene (3.4 g, 19.88 mmol) was dissolved in dimethyl sulfoxide (30 mL), and NaOH solution (1 N, 40 mL, 40 mmol) was added. The mixture was heated to 50° C., and reacted for 3 h. After the reaction, water (100 mL) was added. The mixture was extracted with ethyl acetate (50 mL×3). The organic phases were combined, and concentrated. The residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate=5:1) to get the title compound (2.5 g, yield: 74.4percent).To a stirred solution of 24 (0.63 g, 3.7 mmol) in DMSO (5.3 mL) was added 30percent NaOH (2.5 mL, 18.0 mmol) solution. The mixture was stirred for 21 h at room temperature, cooled to 0 °C and acidified with 6 N HCl. The mixture was pour into 5percent HCl and extracted with ether several times. The combined organic layers were washed with 5percent HCl three times, then with brine, and dried over NaTo a solution of 5-fluoro-2-nitroanisole (11.0 g, 64.3 mmol) in dimethylsulfoxide (30 mL) /water (5 mL) was added sodium hydroxide (5.36 g, 129 mmol), and the mixture was stirred at 9OGeneral procedure: A suspension of 2-methylphenol(18.5 mmol, 1.0 eq) and Cu(NOConcentrated nitric acid (55.83 mg, 886.09 mmol) was added to a solution of trimethoxyphenol (100 mg, 805.54mmol) in acetic acid (2 mL) and stirred at 0 °C for 3 hours. The aqueous phase was extracted with ethyl acetate (20 mL* 2). The combined organic layers were washed with NaCl solution (20 mL * 2), and then dried over sodium sulfate, filtered and evaporated, and the residue was purified by column chromatography to give compound 72A (48 mg, 35.23percent).1H NMR (400MHz, METHANOL-d4) = 10.914 (s, 1H), 7.901 - 7.887(d, 1H), 6.614-6.609 (d, 1H), 6.50- 6.48 (m, 1H), 3.875 (s, 3H)A solution of 3-fluoro-4-nitrophenol (0.5 g, 3.2 mmol) in 0.5M sodium methoxide in methanol (7 mL, 3.5 mmol) was stirred at 50Step 1:To a solution of 3-fluoro-4-nitrophenol (5.00 g, 31.8 mmol) in anhydrous MeOH (100 mL) was added NaOMe (10.2 g, 192 mmol). The reaction mixture was heated atreflux for 72 h, adjusted to pH 6 with 2 M citric acid, and extracted with EtOAc (2 × 500 mL). The organic layers were combined, washed with brine (50 mL), dried over MgSO4, concentrated under reduced pressure and recrystallised with EtOAc to give3-methoxy-4-nitrophenolas a brown powder (4.80 g, 88percent).1H-NMR(DMSO-d6):δ3.86 (s, 3H, CH3), 6.46 (dd, 1H, J= 9.0 & 2.2 Hz, Ph-H), 6.59 (d, 1H, J= 2.3 Hz, Ph-H), 7.89 (d, 1H, J= 9.0 Hz, Ph-H), 10.98 (s, 1H, OH).To a solution of 3-fluoro-4-nitrophenol (3.0 g, 19.0 mmol) in methanol (50 mL) was addedNaOMe (3.09 g, 57.32 mmol). The reaction mass was heated at reflux for 60 h. After thereaction completion, the reaction mass was concentrated, diluted with water, acidified with dil. HC1 and extracted with DCM. The organic portion was dried over Na2504 and concentrated to afford 2.7 g of the title product.’H NMR (300 MHz, DMSO-d6): 10.90 (s, 1H), 7.89-7.86 (d, J = 9.3 Hz, 1H), 6.59 (s, 1H), 6.48-6.45 (d, J = 9.3 Hz, 1H), 3.86 (s, 3H); MS [M-Hj:168.07General procedure: To a solid mixture of phenol (1–3 equiv) and Bi(NO

Molecular Weight:169.13
XLogP3:0.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:169.03750770
Monoisotopic Mass:169.03750770
Topological Polar Surface Area:75.3
Heavy Atom Count:12
Complexity:167
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes