* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 20 h;
A solution of 5-bromo-2-chloro-4-fluorophenol (1.0 g, 4.4 mmol) in DMF (5 mL) and methyl iodide (0.55 mL, 8.8 mmol) were added to potassium carbonate (1.2 g, 8.9 mmol), followed by stirring at room temperature for 20 hours. After the reaction was completed, water (20 mL) was added to the reaction mixture, and the resultant product was extracted with ether (20 mL*3). The organic layer was washed with a saturated saline solution (20 mL), and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure, whereby 5-bromo-2-chloro-4-fluoroanisole (0.951 g, yield: 90percent) was obtained as a white solid. 1H-NMR (400 MHz, CDCl3): δ3.88 (s, 3H), 7.07 (d, J=5.8 Hz, 1H), 7.19 (d, J=8.0 Hz, 1H). 19F-NMR (376 MHz, CDCl3): δ-116.1 (s, 1F).
90%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 20 h;
Potassium carbonate (1.2 g, 8.9 mmol) in 5bromo2chloro4fluorophenol(1.0 g, 4.4 mmol) in DMF (5 mL) solutionand methyl iodide (0.55 mL,. 8 .8mmol) was added, and the mixture was stirred for 20 hours at room temperature.After completion of the reaction, water (20 mL) was added to the reaction mixture and extracted with ether (20mL × 3). Theorganic layer was washed with saturated brine (20 mL), dried over anhydrous magnesium sulfate, and the solvent wasdistilled off under reduced pressure, 5-bromo-2-chloro-4-fluoroanisole as a white solid (0.951 g , yield: 90percent).
90%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 20 h;
Potassium carbonate (1.2g, 8.9mmol), 5-bromo-2-chloro-4-fluorophenol (1.0 g, 4.4 mmol) in DMF (5 mL) solution and methyl iodide (0.55mL, 8.8mmol) was added, and the mixture was stirred for 20 hours at room temperature. After completion of the reaction, water (20 mL) was added to the reaction mixture, and extracted with ether (20mL × 3). The organic layer was washed with saturated brine (20 mL), dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure, 5-bromo-2-chloro-4-fluoroanisole as a white solid (0 .951g,Yield: 90percent).
Reference：
[1] Patent: US2016/24110, 2016, A1, . Location in patent: Paragraph 0577; 0585
[2] Patent: JP2016/56157, 2016, A, . Location in patent: Paragraph 0163
[3] Patent: JP2016/60742, 2016, A, . Location in patent: Paragraph 0242; 0244
To concentrated sulfuric acid (100mL) solution of2-chloro-4-fluoro anisole (38g, 237mmol), bromine (19mL, 737mmol) was addedunder ice-cooling, and the mixture was stirred for 1.5 hours. the reactionsolution was added gradually into ice water and extracted with diethyl ether(300mL × 3). After washing the organic layer with 5percent aqueous sodium thiosulfatesolution (300 mL), the organic layer was dried over anhydrous magnesiumsulfate, filtered, and the crude product obtained through concentration underreduced pressure was purified by silica gel chromatography (hexane: ethylacetate = 1 : 0~10: 1) to give white solid of 5-bromo-2-chloro-4-fluoro anisole(8.0 g, yield: 14percent) and white solid of 2-bromo-6-chloro-4- fluoro anisole (16.7g, yield: 30percent).
14%
for 1.5 h; Cooling with ice
2-chloro-4-fluoroanisole (38g, 237mmol) concentrated sulfuric acid (100mL) solution, bromine (19mL, 737mmol) was added under ice-cooling, and the mixture was stirred for 1.5 hours. It was added to the reaction solution gradually into ice water, and extracted with diethyl ether (300mL × 3). After washing the organic layer with 5percent aqueous sodium thiosulfate solution (300 mL), the organic layer was dried over anhydrous magnesium sulfate, filtered, and the crude product obtained through concentration under reduced pressure by silica gel chromatography - (hexane: ethyl acetate = 1 : 0 to 10: 1) to give 5-bromo-2-chloro-4-fluoroanisole of a white solid (8.0g, yield: 14percent) and 2-bromo-6-chloro-4-fluoroanisole of a white solid (16.7g, yield: 30percent)It was obtained.
14%
for 1.5 h; Cooling with ice
Reference Example-3 Bromine (19 mL, 31 mmol) was added to a solution of 2-chloro-4-fluoroanisole (38 g, 24 mmol) in concentrated sulfuric acid (100 mL) under ice-cooling, followed by stirring for 1.5 hours. The reaction solution was added little by little to ice water, and the resultant product was extracted with ether (300 mL*3). After the organic layer was washed with a 5percent sodium thiosulfate aqueous solution (300 mL), the organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure, and the obtained crude product was purified by silica gel chromatography (hexane:ethyl acetate=1:0 to 10:1), whereby 5-bromo-2-chloro-4-fluoroanisole (8.0 g, yield: 14percent) was obtained as a white solid, and 2-bromo-6-chloro-4-fluoroanisole (16.7 g, yield: 24percent) was obtained as a white solid. 5-Bromo-2-chloro-4-fluoroanisole: 1H-NMR (400 MHz, CDCl3): δ3.88 (s, 3H), 7.07 (d, J=6.0 Hz, 1H), 7.19 (d, J=7.8 Hz, 1H). 19F-NMR (376 MHz, CDCl3): δ-116.1 (s, 1F).
Reference：
[1] Patent: JP2016/56157, 2016, A, . Location in patent: Paragraph 0160
[2] Patent: JP2016/60742, 2016, A, . Location in patent: Paragraph 0240
[3] Patent: US2016/24110, 2016, A1, . Location in patent: Paragraph 0425; 0426
5
[ 1996-41-4 ]
[ 146447-18-9 ]
Reference：
[1] Patent: US2016/24110, 2016, A1,
[2] Patent: JP2016/56157, 2016, A,
[3] Patent: JP2016/60742, 2016, A,
6
[ 167415-27-2 ]
[ 146447-18-9 ]
Reference：
[1] Patent: US2016/24110, 2016, A1,
[2] Patent: JP2016/56157, 2016, A,
[3] Patent: JP2016/60742, 2016, A,
7
[ 399-94-0 ]
[ 146447-18-9 ]
Reference：
[1] Patent: US2016/24110, 2016, A1,
[2] Patent: JP2016/56157, 2016, A,
[3] Patent: JP2016/60742, 2016, A,
8
[ 153406-19-0 ]
[ 146447-18-9 ]
Reference：
[1] Patent: US2016/24110, 2016, A1,
[2] Patent: JP2016/56157, 2016, A,
[3] Patent: JP2016/60742, 2016, A,
9
[ 153471-75-1 ]
[ 146447-18-9 ]
Reference：
[1] Patent: US2016/24110, 2016, A1,
[2] Patent: JP2016/56157, 2016, A,
[3] Patent: JP2016/60742, 2016, A,
10
[ 137110-49-7 ]
[ 146447-18-9 ]
Reference：
[1] Patent: US2016/24110, 2016, A1,
[2] Patent: JP2016/56157, 2016, A,
[3] Patent: JP2016/60742, 2016, A,
11
[ 2267-25-6 ]
[ 146447-18-9 ]
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 19, p. 5206 - 5208
With sodium t-butanolate;palladium diacetate; In toluene;
1.0 g (4.2 mmol) of 5-Bromo-2-chloro-4-fluoroanisole, 47 mg (0.21 mmol) of palladium acetate, 180 mg (0.29 mmol) of binap, 0.65 g (6.7 mmol) of sodium tert-butoxide, and 3.6 g (42 mmol) of piperazine in 3 mL of dry toluene werw heated at 110 C. for 24 hours. The reaction was partitioned between ethyl acetate and water, and the phases were separated. The ethyl acetate phase was washed once each with water and brine, and was concnentrated. The residue was purified by chromatography to give 1-(4-Chloro-2-fluoro-5-methoxy-phenyl)-piperazine.
3-fluoro-2-phenylsulfinyl1-5-trifluoromethylpyridine[ No CAS ]
[ 216751-65-4 ]
Yield
Reaction Conditions
Operation in experiment
With magnesium; In tetrahydrofuran; hydrogenchloride; sodium hydroxide; dichloromethane;
EXAMPLE 6 3-Fluoro-2-(4-chloro-2-fluoro-5-methoxyphenyl)-5-trifluoromethylpyridine [Table 1, Ia. 1] A Grignard solution, prepared from 16.96 g (0.0708 mol) of <strong>[146447-18-9]1-bromo-4-chloro-2-fluoro-5-methoxybenzene</strong> and 1.98 g (0.0813 mol) of magnesium turnings in 60 ml of THF was added with stirring and gentle cooling at 24-36 C. to a solution of 17.8 g (0.0616 mol) of 3-fluoro-2-phenylsulfinyl1-5-trifluoromethylpyridine in 45 ml of THF over a period of 20 min. The reaction mixture was stirred at 24 C. for 4 h and then concentrated under reduced pressure, taken up in methylene chloride and extracted in succession with 1 N hydrochloric acid, 1 N of aqueous sodium hydroxide solution and with water and then concentrated. The residue was stirred in 1 N of aqueous sodium hydroxide solution for 45 min at 95 C. and then concentrated to a quarter of its volume at 300 mbar. The residue was partitioned between methylene chloride and water and the organic phase was dried, filtered off with suction through silica gel and concentrated under reduced pressure. 8.7 g (43.7% of theory) of the title compound of mp. 79-80 C. were obtained.
3. Preparation of l-bromo-4-chloro-2-fluoro-5-methoxybenzene; A solution of 4-chloro-2-fluoro-5-methoxyaniline (25.0 g, 0.143 mol) in 10 percent HBr (250 mL) was cooled to 0 C and a solution of sodium nitrite (15.0 g, 0.218 mol) in water (20 mL) was slowly added. After addition, methylene chloride (50 mL) and cupric bromide (30.0 g, 0.244 mol) were added slowly. The reaction mixture was then warmed to ambient temperature, stirred for one hour, filtered through a bed of celite, and extracted with methylene chloride (2 x 100 mL). The combined organic phases were dried and concentrated. Chromatography of the dark oil (5 percent ethyl acetate in hexanes) gave 1- bromo-4-chloro-2-fluoro-5-methoxybenzene (16.6 g, 0.070 mol): 1HNMR (CDCl3): delta 7.20 (m, IH), 7.05 (dd, IH), 4.00 (s, 3H).
With hydrogen bromide; copper(ll) bromide; sodium nitrite; In dichloromethane; water; at 0 - 20℃; for 1h;
3. Preparation of 1-bromo-4-chloro-2-fluoro-5-methoxybenzene; A solution of 4-chloro-2-fluoro-5-methoxyaniline (25.0 g, 0.143 mol) in 10% HBr (250 mL) was cooled to 0 C. and a solution of sodium nitrite (15.0 g, 0.218 mol) in water (20 mL) was slowly added. Methylene chloride (50 mL) and curpric bromide (30.0 g, 0.244 mol) were added slowly and then the mixture was warmed to ambient temperature and stirred for 1 hour. The reaction mixture was filtered through a bed of celite and extracted with methylene chloride (2×100 mL) and the combined organic phases were dried (sodium sulfate) and concentrated. Chromatography of the dark oil (5% ethyl acetate in hexanes) gave 1-bromo-4-chloro-2-fluoro-5-methoxybenzene (16.6 g, 0.070 mol): 1H NMR (CDCl3): delta 7.20 (m, 1H) 7.05 (dd, 1H), 4.00 (s, 3H).
3.0 g (17.1 mmol) of 4-Chloro-2-fluoro-5-methoxy-aniline in 23 mL of hydrobromic acid and 23 mL of water, and the solution was cooled to 0 C. To this was added 1.5 g (21.4 mmol) of sodium nitrite in 2 mL of water. 9 g (36 mmol) of copper bromide was added in 30 mL of 50% hydrobromic acid. After the addition, the mixture was heated to 55 C. for one hour. The mixture was cooled, and was extracted with ethyl acetate. The ethyl acetate phase was washed once each with water and brine, and was concentrated to give 5-Bromo-2-chloro-4-fluoroanisole.
ethyl 2-(4-chloro-2-fluoro-5-methoxyphenyl)-2-oxoacetate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
72%
To THF (40mL) solution of5-bromo-2-chloro-4-fluoro anisole (9.23g, 38.5mmol), isopropyl magnesium chloride solution(20.2mL, 2M-THF solution) was added at -40 ,and was stirred at room temperature for 30 minutes. THFsolution of the obtained Grignard reagent was dropped at -40 toTHF (5mL) solution of diethyl oxalate (5.06mL, 36.6mmol),and the mixture was stirred for one hour at 0 .Saturated ammonium chloride solution (50mL)was added to the reaction solution, and extracted with ethyl acetate (100mL ×3). The organic layer was dried over anhydrous magnesium sulfate, then thecrude product obtained by concentrating under reduced pressure was eluted bysilica gel column chromatography (hexane: ethyl acetate = 10: 1) and colorlessliquid of 2- (4-chloro-2-fluoro - 5-methoxyphenyl) -2-oxo ethyl acetate (7.24 g,yield: 72%) was obtained.
72%
<strong>[146447-18-9]5-bromo-2-chloro-4-fluoroanisole</strong> (9.23 g, 38.5 mmol) in THF (40 mL) solution of isopropylmagnesium chloride solution (20.2mL, 2M-THF solution) at -40 C It was added and stirred for 30 minutes at room temperature. Obtained mixture THF solution, diethyl oxalate (5.06mL, 36.6mmol) was dropped at -40C in THF (5mL) solution, and the mixture was stirred for one hour at 0C . Saturated ammonium chloride solution (50mL) was added to the reaction solution, and extracted with ethyl acetate (100mL × 3). The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure to give crude product was purified by silica gel column chromatography -eluted with (hexane: ethyl acetate = 10: 1) ethyl-2-(4-chloro-2-fluoro-5-methoxyphenyl)-2-oxoacetate colorless liquid (7.24 g, yield: 72%) was obtained
68%
Reference Example-26 After THF (25 mL) was added to magnesium (2.55 g, 105 mmol) at room temperature, iodine (10 mg) was added thereto, then, a solution of <strong>[146447-18-9]5-bromo-2-chloro-4-fluoroanisole</strong> (23.9 g, 100 mmol) in THF (50 mL) was slowly added thereto, and the resultant product was stirred for 1 hour, whereby a Grignard reagent was prepared. The Grignard reagent was added dropwise to a solution of diethyl oxalate (14.5 mL, 105 mmol) in THF (14.5 mL) at -40 C. or lower. After the dropping was completed, the temperature of the reaction solution was raised to 0 C., followed by stirring 1 hour. After the reaction was completed, a saturated ammonium chloride aqueous solution (100 mL) was added to the reaction solution, and the resultant product was diluted with water (100 mL) and extracted with ethyl acetate (200 L*2). After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The crude product was distilled under reduced pressure (125 C. to 130 C./4 mmHg), whereby ethyl 2-(4-chloro-2-fluoro-5-methoxyphenyl)-2-oxoacetate (17.8 g, yield: 68%) was obtained as a pale yellow oily material. 1H-NMR (400 MHz, CDCl3): delta1.40 (t, J=7.2 Hz, 3H). 3.95 (s, 3H), 4.43 (q, J=7.2 Hz, 2H), 7.25 (d, J=9.9 Hz, 1H), 7.42 (d, J=5.9 Hz, 1H). 19F-NMR (376 MHz, CDCl3): delta-119.7 (s, 1F).
With sulfuric acid; bromine; for 1.5h;Cooling with ice;
To concentrated sulfuric acid (100mL) solution of2-chloro-4-fluoro anisole (38g, 237mmol), bromine (19mL, 737mmol) was addedunder ice-cooling, and the mixture was stirred for 1.5 hours. the reactionsolution was added gradually into ice water and extracted with diethyl ether(300mL × 3). After washing the organic layer with 5% aqueous sodium thiosulfatesolution (300 mL), the organic layer was dried over anhydrous magnesiumsulfate, filtered, and the crude product obtained through concentration underreduced pressure was purified by silica gel chromatography (hexane: ethylacetate = 1 : 0~10: 1) to give white solid of 5-bromo-2-chloro-4-fluoro anisole(8.0 g, yield: 14%) and white solid of 2-bromo-6-chloro-4- fluoro anisole (16.7g, yield: 30%).
14%; 30%
With sulfuric acid; bromine; for 1.5h;Cooling with ice;
2-chloro-4-fluoroanisole (38g, 237mmol) concentrated sulfuric acid (100mL) solution, bromine (19mL, 737mmol) was added under ice-cooling, and the mixture was stirred for 1.5 hours. It was added to the reaction solution gradually into ice water, and extracted with diethyl ether (300mL × 3). After washing the organic layer with 5% aqueous sodium thiosulfate solution (300 mL), the organic layer was dried over anhydrous magnesium sulfate, filtered, and the crude product obtained through concentration under reduced pressure by silica gel chromatography - (hexane: ethyl acetate = 1 : 0 to 10: 1) to give 5-bromo-2-chloro-4-fluoroanisole of a white solid (8.0g, yield: 14%) and 2-bromo-6-chloro-4-fluoroanisole of a white solid (16.7g, yield: 30%)It was obtained.
14%; 24%
With sulfuric acid; bromine; for 1.5h;Cooling with ice;
Reference Example-3 Bromine (19 mL, 31 mmol) was added to a solution of 2-chloro-4-fluoroanisole (38 g, 24 mmol) in concentrated sulfuric acid (100 mL) under ice-cooling, followed by stirring for 1.5 hours. The reaction solution was added little by little to ice water, and the resultant product was extracted with ether (300 mL*3). After the organic layer was washed with a 5% sodium thiosulfate aqueous solution (300 mL), the organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure, and the obtained crude product was purified by silica gel chromatography (hexane:ethyl acetate=1:0 to 10:1), whereby 5-bromo-2-chloro-4-fluoroanisole (8.0 g, yield: 14%) was obtained as a white solid, and 2-bromo-6-chloro-4-fluoroanisole (16.7 g, yield: 24%) was obtained as a white solid. 5-Bromo-2-chloro-4-fluoroanisole: 1H-NMR (400 MHz, CDCl3): delta3.88 (s, 3H), 7.07 (d, J=6.0 Hz, 1H), 7.19 (d, J=7.8 Hz, 1H). 19F-NMR (376 MHz, CDCl3): delta-116.1 (s, 1F).
With potassium carbonate; In N,N-dimethyl-formamide; at 20.0℃; for 20.0h;
A solution of 5-bromo-2-chloro-4-fluorophenol (1.0 g, 4.4 mmol) in DMF (5 mL) and methyl iodide (0.55 mL, 8.8 mmol) were added to potassium carbonate (1.2 g, 8.9 mmol), followed by stirring at room temperature for 20 hours. After the reaction was completed, water (20 mL) was added to the reaction mixture, and the resultant product was extracted with ether (20 mL*3). The organic layer was washed with a saturated saline solution (20 mL), and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure, whereby 5-bromo-2-chloro-4-fluoroanisole (0.951 g, yield: 90%) was obtained as a white solid. 1H-NMR (400 MHz, CDCl3): delta3.88 (s, 3H), 7.07 (d, J=5.8 Hz, 1H), 7.19 (d, J=8.0 Hz, 1H). 19F-NMR (376 MHz, CDCl3): delta-116.1 (s, 1F).
90%
With potassium carbonate; In N,N-dimethyl-formamide; at 20.0℃; for 20.0h;
Potassium carbonate (1.2 g, 8.9 mmol) in 5bromo2chloro4fluorophenol(1.0 g, 4.4 mmol) in DMF (5 mL) solutionand methyl iodide (0.55 mL,. 8 .8mmol) was added, and the mixture was stirred for 20 hours at room temperature.After completion of the reaction, water (20 mL) was added to the reaction mixture and extracted with ether (20mL × 3). Theorganic layer was washed with saturated brine (20 mL), dried over anhydrous magnesium sulfate, and the solvent wasdistilled off under reduced pressure, 5-bromo-2-chloro-4-fluoroanisole as a white solid (0.951 g , yield: 90%).
90%
With potassium carbonate; In N,N-dimethyl-formamide; at 20.0℃; for 20.0h;
Potassium carbonate (1.2g, 8.9mmol), 5-bromo-2-chloro-4-fluorophenol (1.0 g, 4.4 mmol) in DMF (5 mL) solution and methyl iodide (0.55mL, 8.8mmol) was added, and the mixture was stirred for 20 hours at room temperature. After completion of the reaction, water (20 mL) was added to the reaction mixture, and extracted with ether (20mL × 3). The organic layer was washed with saturated brine (20 mL), dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure, 5-bromo-2-chloro-4-fluoroanisole as a white solid (0 .951g,Yield: 90%).
5-chloro-4-[4-chloro-2-fluoro-5-[[3-(2-chloro-4-fluorophenyl)-5-methyl-2-isoxazolin-5-yl]methyloxy]phenyl]-1,2-tetramethylene-4-pyrazolin-3-one[ No CAS ]
With copper(l) chloride; copper dichloride; isopentyl nitrite; In acetonitrile; at 20℃; for 4h;
A solution of isoamyl nitrite (17.6 mL, 126 mmol) in acetonitrile (60 mL) was added dropwise to a solution of 4-bromo-5-fluoro-2-methoxyaniline (9.2 g, 41.8 mmol), copper(I) chloride (8.28 g, 83.6 mmol), and copper(II) chloride (16.86 g, 125 mmol) in acetonitrile (200 mL) at room temperature. The mixed solution was stirred at room temperature for 4 hours, and poured into 2N hydrochloric acid (100 mL), and the resultant product was extracted with ethyl acetate (50 mL*3). The organic layer was washed with a saturated saline solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure, whereby a crude product was obtained as a brown solid. This was purified by silica gel column (hexane), whereby 5-bromo-2-chloro-4-fluoroanisole (6.6 g, yield: 66%) was obtained as a white solid. 1H-NMR (400 MHz, CDCl3): delta3.88 (s, 3H), 7.07 (d, J=5.8 Hz, 1H), 7.19 (d, J=8.0 Hz, 1H). 19F-NMR (376 MHz, CDCl3): delta-116.1 (s, 1F).
66%
With copper(l) chloride; copper dichloride; isopentyl nitrite; In acetonitrile; at 20℃; for 4h;
To acetonitrile (200mL) solution of 4-bromo-5-fluoro-2-methoxyaniline(9.2g, 41.8mmol), copper chloride (I) (8.28g, 83.6mmol) and copper (II)chloride (16.86g, 125mmol), acetonitrile (60mL) solution of isoamyl nitrite(17.6mL, 126mmol) was added dropwise at room temperature. After the mixed solutionwas stirred for 4 hours at room temperature, it was poured into 2N hydrochloricacid (100 mL), and extracted with ethyl acetate (50mL × 3). The organic layerwas washed with saturated brine, dried over anhydrous magnesium sulfate, andthe solvent was evaporated under reduced pressure to obtain a crude product ofbrown solid. By purifying this product by a silica gel column (hexane), whitesolid (6.6 g, yield: 66%) of 5-bromo-2-chloro-4- fluoro anisole was obtained.
66%
With copper(l) chloride; copper dichloride; In acetonitrile; at 20℃; for 4h;
4-bromo-5-fluoro-2-methoxyaniline (9.2g, 41.8mmol), copper chloride (I) (8.28g, 83.6mmol) and copper (II) chloride (16.86g, 125mmol) in acetonitrile (200 mL) solution of isoamyl nitrite at room temperature (17. 6 mL, was added dropwise acetonitrile (60 mL) solution of 126 mmol). After the mixed solution was stirred for 4 hours at room temperature, poured into 2N hydrochloric acid (100 mL), and extracted with ethyl acetate (50mL × 3). The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product of a brown solid. By purifying this product by a silica gel column (hexane), 5-bromo-2-chloro-4-fluoroanisole as a white solid (6.6 g, yield: 66%) was obtained
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