392-71-2|2,6-Dichloro-4-fluorophenol| Ambeed

CAS No. :	392-71-2
Formula :	C₆H₃Cl₂FO
M.W :	180.99
SMILES Code :	OC1=C(Cl)C=C(F)C=C1Cl
MDL No. :	MFCD00010675
InChI Key :	BOJVIFKSTRCIRJ-UHFFFAOYSA-N
Pubchem ID :	94950

Safety of [ 392-71-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Application In Synthesis of [ 392-71-2 ]

* 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.

Downstream synthetic route of [ 392-71-2 ]

[ 392-71-2 ] Synthesis Path-Downstream 1~54

1
[ 371-41-5 ]
[ 392-71-2 ]

References: [1]Journal of the Chemical Society,1930,p. 1870.
[2]Journal of the American Chemical Society,1959,vol. 81,p. 94,95, 97.

2
[ 392-71-2 ]
[ 697-91-6 ]

References: [1]Journal of the Chemical Society,1930,p. 1870.

3
[ 392-71-2 ]
[ 79-11-8 ]
[ 392-17-6 ]

References: [1]Journal of the American Chemical Society,1959,vol. 81,p. 94,95, 97.

4
[ 392-71-2 ]
[ 77-78-1 ]
[ 392-24-5 ]

References: [1]Journal of the Chemical Society,1930,p. 1868,2166, 2168.

5
[ 4227-95-6 ]
[ 392-71-2 ]
[ 117923-76-9 ]

References: [1]Canadian Journal of Chemistry,1988,vol. 66,p. 1635 - 1640.

6
[ 392-71-2 ]
[ 54904-42-6 ]
[ 100-02-7 ]
2,6-Cl₂-4-FC₆H₂OHgPh [ No CAS ]

References: [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1975,vol. 24,p. 2334 - 2339.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1975,vol. 24,p. 2447 - 2453.

7
[ 392-71-2 ]
[ 75-03-6 ]
[ 1026397-39-6 ]

Yield	Reaction Conditions	Operation in experiment
64.9%		To a solution of 2,6-dichloro-4-fluoro-phenol (2 g, 11 .11 mmol) in 20 mL anhydrous DMF was added K2003 (3.07 g, 22.22 mmol) at room temperature. After stirring for 30 mi EtI (3.47 g, 22.22 mmol) was added and the mixture was stirred at room temperature overnight. Waterwas added and the product was extracted with MTBE. The organic phase was washed with brine, dried and concentrated in vacuum to give the crude product, which was purified by column chromatography eluted with 100 % cyclohexane to afford 1 ,3-dichloro-2-ethoxy-5-fluoro- benzene (1 .5 g, 64.9 %).1H NMR (0D013, 400MHz): ö 1.46 (t, J=7.03 Hz, 3 H) 4.07 (q, J=7.03 Hz, 2 H) 7.07 (d, J=7.78 Hz, 2 H).

References: [1]Patent: WO2015/7564,2015,A1 .Location in patent: Page/Page column 147.
[2]Journal of Medicinal Chemistry,1996,vol. 39,p. 4261 - 4274.

8
[ 392-71-2 ]
[ 79-22-1 ]
[ 183325-41-9 ]

References: [1]Chemical and Pharmaceutical Bulletin,1996,vol. 44,p. 1663 - 1668.

9
[ 371-41-5 ]
aqueous NaOCl [ No CAS ]
[ 392-71-2 ]

References: [1]Journal of the Chemical Society,1930,p. 1870.

11
[ 392-71-2 ]
[ 7697-37-2 ]
[ 697-91-6 ]

References: [1]Journal of the Chemical Society,1930,p. 1870.

12
[ 392-71-2 ]
[ 77-78-1 ]
aqueous NaOH [ No CAS ]
[ 392-24-5 ]

References: [1]Journal of the Chemical Society,1930,p. 2166,2168.

13
[ 56-23-5 ]
[ 392-71-2 ]
[ 77-78-1 ]
K₂CO₃ [ No CAS ]
[ 392-24-5 ]

References: [1]Journal of the Chemical Society,1930,p. 2166,2168.

14
[ 392-71-2 ]
[ 116133-09-6 ]
4-[4-chloro-6-(2,6-dichloro-4-fluoro-phenoxy)-[1,3,5]triazin-2-ylamino]-benzonitrile [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2229 - 2234.

15
[ 392-71-2 ]
methyl 8-bromo-3,7-dimethyl-2,4,6-octatrienoate [ No CAS ]
[ 538315-13-8 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 1931 - 1939.

16
[ 392-71-2 ]
[ 96-32-2 ]
[ 353556-76-0 ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2115 - 2137.

17
[ 392-71-2 ]
[ 392-17-6 ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2115 - 2137.

18
[ 392-71-2 ]
2-(2,6-dichloro-4-fluoro-phenoxy)-N-pyridin-4-yl-acetamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2115 - 2137.

19
[ 392-71-2 ]
2-(2,6-dichloro-4-fluoro-phenoxy)-N-(1H-indazol-5-yl)-acetamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2115 - 2137.

20
[ 392-71-2 ]
2-(2,6-dichloro-4-fluoro-phenoxy)-N-(1H-indazol-6-yl)-acetamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2115 - 2137.

21
[ 392-71-2 ]
(2E,4E,6E)-8-(2,6-Dichloro-4-fluoro-phenoxy)-3,7-dimethyl-octa-2,4,6-trienoic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 1931 - 1939.

22
[ 392-71-2 ]
[ 183325-43-1 ]

References: [1]Chemical and Pharmaceutical Bulletin,1996,vol. 44,p. 1663 - 1668.

23
[ 392-71-2 ]
[ 1026303-49-0 ]

References: [1]Chemical and Pharmaceutical Bulletin,1996,vol. 44,p. 1663 - 1668.
[2]Chemical and Pharmaceutical Bulletin,1996,vol. 44,p. 1663 - 1668.

24
[ 392-71-2 ]
[ 183325-42-0 ]

References: [1]Chemical and Pharmaceutical Bulletin,1996,vol. 44,p. 1663 - 1668.

25
[ 392-71-2 ]
[ 183325-44-2 ]

References: [1]Chemical and Pharmaceutical Bulletin,1996,vol. 44,p. 1663 - 1668.
[2]Chemical and Pharmaceutical Bulletin,1996,vol. 44,p. 1663 - 1668.

26
[ 392-71-2 ]
[ 183325-45-3 ]

References: [1]Chemical and Pharmaceutical Bulletin,1996,vol. 44,p. 1663 - 1668.
[2]Chemical and Pharmaceutical Bulletin,1996,vol. 44,p. 1663 - 1668.

27
[ 392-71-2 ]
2-tert-butyl-5,7-dichloro-4-methoxycarbonyl-6-methoxycarbonyloxy-4H-1,4-benzoxazine [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1996,vol. 44,p. 1663 - 1668.
[2]Chemical and Pharmaceutical Bulletin,1996,vol. 44,p. 1663 - 1668.

28
[ 392-71-2 ]
2-tert-butyl-5,7-dichloro-4-ethoxycarbonyl-6-methoxycarbonyloxy-4H-1,4-benzoxazine [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1996,vol. 44,p. 1663 - 1668.
[2]Chemical and Pharmaceutical Bulletin,1996,vol. 44,p. 1663 - 1668.

29
[ 392-71-2 ]
2,4-Dichloro-3-ethoxy-6-fluoro-benzaldehyde [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4261 - 4274.

30
[ 392-71-2 ]
[ 1027174-56-6 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4261 - 4274.

31
[ 392-71-2 ]
[ 1026367-39-4 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4261 - 4274.

32
[ 392-71-2 ]
1-(5-Bromo-pyridin-2-yl)-3-[2-(2,4-dichloro-3-ethoxy-6-fluoro-phenyl)-ethyl]-thiourea [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4261 - 4274.

33
[ 371-40-4 ]
[ 392-71-2 ]

References: [1]Journal of the American Chemical Society,1959,vol. 81,p. 94,95, 97.

34
[ 392-71-2 ]
[ 105-36-2 ]
[ 392-17-6 ]

Yield	Reaction Conditions	Operation in experiment
72.8%		The mixture of <strong>[392-71-2]2,6-dichloro-4-fluorophenol</strong> (362 mg, 2.0 mmol), potassium carbonate (910 mg, 6.6 mmol), ethyl bromoacetate (500 mg, 3.0 mmol) and acetone (25 ml) was refluxed for 12 h. After cooling, the mixture was filtered to remove potassium carbonate. The filtrate was concentrated under reduced pressure. To this residue, 10 ml dioxane and 14 ml 5% sodium hydroxide solution were added. After the mixture was stirred at room temperature overnight, it was acidified with concentrated hydrochloric acid to pH 2, and then extracted three times with ethyl acetate (15 ml each). Organic phases were combined, washed with water and brine, dried over magnesium sulfate, filtered, and then evaporated in vacuo. The residue was recrystallized from ethyl acetate and petroleum ether to give 348 mg 2,6-dichloro-4-fluorophenoxyacetic acid as white crystals, mp 155-158 C., yield: 72.8%. The chemical structure analysis was performed by 1HNMR (Acetone-d6, 600 MHz): δ 7.36 (m, 2H, Ar-H), 4.67 (s, 2H, OCH2CO).

References: [1]Patent: US6350756,2002,B1 .Location in patent: Page column 43.

35
[ 87-65-0 ]
N-fluoro-2-chloro-6-(trichloromethyl) pyridinium [ No CAS ]
[ 79-00-5 ]
[ 392-71-2 ]

Yield	Reaction Conditions	Operation in experiment
		Example 5. Preparation of 4-Fluoro-2,6-dichlorophenol A mixture of 082 g of 2,6-dichlorophenol, 1.67 g of N-fluoro-2-chloro-6-(trichloromethyl) pyridinium rfluoroborate, and 40 ml of 1,1,2-trichloroethane was placed in a 100 ml 3-necked round bottomed flask equipped with a magnetic stirring bar, a thermometer, and a reflux condenser. The mixture was heated to 55 C. and allowed to react at that temperature for 8 hours under nitrogen. The mixture was then allowed to cool. Analysis by standardized gas-liquid chromatography using a mass spectrometer detector indicated that the title product was present in 24 percent conversion. The product identity was confirmed by its known 19F and 1 H NMR spectra.

References: [1]Patent: US5116982,1992,A .

36
(rac.)-(3aR*,6aR*)-6-[cyclopropyl-(2,3-dimethyl-benzyl)-carbamoyl]-5-[4-(2-hydroxy-ethyl)-phenyl]-3,3a,4,6a-tetrahydro-1H-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester [ No CAS ]
[ 392-71-2 ]
C₃₉H₄₃Cl₂FN₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine; In toluene; at 100℃; for 1.0h;	2,6-Dichloro-4-fluoro-phenol (39 mg, 0.227 mmol), compound H4 (100 mg, 0.189 mmol) and azodicarboxylic dipiperidide (58 mg, 0.227 mmol) were dissolved in toluene (2 mL), followed by the addition of PBu3 (85%, 54 mg, 0.227 mmol) via syringe under an inert atmosphere. The reaction mixture was heated to 100 0C for 1 h, cooled to rt and Et2O (5 mL) was added. The precipitate was filtered off, the filtrate diluted with EtOAc (10 mL), and the mixture was washed with aq. IM HCl. The org. layer was dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. The crude Boc-protected intermediate of type F was dissolved in a 1:1 mixture of CH3CN/HCO2H, and the mixture was purified by prep. HPLC. The fractions were analyzed and concentrated. The purified Boc-protected intermediate of type F was dissolved in dioxane (0.5 mL), and a sol. of HCl in dioxane (4M, 1 mL) was added. The mixture was shaken for 1 h and then concentrated under reduced pressure. The product was dried under high vacuum to give the title compound (61 mg, 54 % over two steps). LC-MS: tR = 0.97 min; ES+: 593.12.

References: [1]Patent: WO2007/49224,2007,A1 .Location in patent: Page/Page column 45-46.

37
[ 1097776-25-4 ]
[ 392-71-2 ]
[ 1097776-84-5 ]

Yield	Reaction Conditions	Operation in experiment
65%	With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at 90℃; for 0.166667h;Microwave irradiation;	Methyl 3-[5-([3-(hydroxymethyl)-5-(l-methylethyl)-4-isoxazolyl]methyl}oxy)-lH- indol-l-yl]methyl}benzoate (prepared by the general procedure described in Example If) (0.1 g, 0.230 mmol), <strong>[392-71-2]2,6-dichloro-4-fluorophenol</strong> (0.0417 g, 0.230 mmol) and triphenylphosphine (0.06 g, 0.23 mmol) were stirred in toluene (2.5 mL), then diisopropyl azodicarboxylate (0.045 mL, 0.23 mmol) was added to the reaction mixture. The reaction mixture was heated in the microwave at 90 0C for 10 min. The reaction mixture was concentrated and the crude oil was purified by flash chromatography over silica using a hexanes: ethyl acetate gradient of 0 to 30% ethyl <n="128"/>acetate to afford 0.090 g (65%) of methyl 3-[5-([3-[(2,6-dichloro-4- fluorophenyl)oxy]methyl} -5-( 1 -methylethyl)-4-isoxazolyl]methyl} oxy)- lH-indol- 1 - yl]methyl}benzoate. 1H NMR (400 MHz, DMSO-J6): δ 7.81 (d, J = 7 Hz, IH), 7.75 (s, IH), 7.52 (d, J = 8 Hz, 2H), 7.47 (m, IH), 7.41 (m, 2H), 7.29 (d, J = 9 Hz, IH), 7.15 (d, J = 2 Hz, IH), 6.75 (dd, J = 9, 3 Hz, IH), 6.39 (d, J = 3 Hz, IH), 5.45 (s, 2H), 5.07 (s, 2H), 5.03 (s, 2H), 3.78 (s, 3H), 3.35 (m, IH), 1.21 (d, J = 7 Hz, 6H).

References: [1]Patent: WO2009/5998,2009,A1 .Location in patent: Page/Page column 126-127.

38
C₂₄H₂₄ClNO₅ [ No CAS ]
[ 392-71-2 ]
C₃₀H₂₅Cl₃FNO₅ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2969 - 2973.

39
[ 1149624-89-4 ]
[ 392-71-2 ]
C₄₀H₃₉Cl₇FN₃O₅ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 3689 - 3702.

40
[ 1149624-90-7 ]
[ 392-71-2 ]
C₃₉H₃₇Cl₇FN₃O₆ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 3689 - 3702.

41
[ 392-71-2 ]
[ 141699-55-0 ]
[ 1266334-31-9 ]