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CAS No. : | 28342-75-8 | MDL No. : | MFCD08458122 |
Formula : | C6H2Br2F2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PPUZKAPOPPRMFE-UHFFFAOYSA-N |
M.W : | 271.88 | Pubchem ID : | 10564511 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 41.76 |
TPSA : | 0.0 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.47 cm/s |
Log Po/w (iLOGP) : | 2.37 |
Log Po/w (XLOGP3) : | 3.5 |
Log Po/w (WLOGP) : | 4.33 |
Log Po/w (MLOGP) : | 4.63 |
Log Po/w (SILICOS-IT) : | 4.05 |
Consensus Log Po/w : | 3.78 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.17 |
Solubility : | 0.0182 mg/ml ; 0.0000669 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -3.18 |
Solubility : | 0.178 mg/ml ; 0.000656 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.66 |
Solubility : | 0.00595 mg/ml ; 0.0000219 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 1.8 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With bromine; iron In dichloromethane at 20℃; | Preparation 131 ,5-dibromo-2,4-difluorobenzeneTo a solution of l-bromo-2,4-difluorobenzene (19.3 mL, 171 mmol) in CH2CI2 (100 mL) was added iron (3.15 g,56 mmol). To this stirred suspension was added a solution of bromine (1 1 mL, 214 mmol) in CH2CI2 (25 mL) drop wise over 30 min. The resulting mixture was stirred at rt overnight. The reaction mixture was slowly poured into saturated aqueous Na2S203 (200 mL), and the resulting mixture was stirred at rt for 30 min. This was extracted with CH2C12 (3 x 80 mL). The combined extracts were washed with brine, dried over MgS04, filtered and concentrated in vacuo to give 1,5-dibromo- 2,4-difluorobenzene (40 g, 86 percent yield) as a brown oil. XH NMR (500 MHz,CHLOROFORM-d) δ 7.79 (t, J=7.0 Hz, 1H), 7.00 (t, J=8.2 Hz, 1H). |
86% | With bromine; iron In dichloromethane at 20℃; | Preparation 1 1 ,5-dibromo-2,4-difluorobenzene To a solution of l-bromo-2,4-difluorobenzene (19.3 mL, 171 mmol) in CH2CI2 (100 mL) was added iron (3.15 g,56 mmol). To this stirred suspension was added a solution of bromine (1 1 mL, 214 mmol) in CH2CI2 (25 mL) drop wise over 30 min. The resulting mixture was stirred at rt overnight. The reaction mixture was slowly poured into saturated aqueous Na2S203 (200 mL), and the resulting mixture was stirred at rt for 30 min. This was extracted with CH2C12 (3 x 80 mL). The combined extracts were washed with brine, dried over MgS04, filtered and concentrated in vacuo to give 1,5-dibromo- 2,4-difluorobenzene (40 g, 86 percent yield) as a brown oil. XH NMR (500 MHz, CHLOROFORM-d) δ 7.79 (t, J=7.0 Hz, 1H), 7.00 (t, J=8.2 Hz, 1H). |
84% | at 60℃; for 5 h; | 39 mmol (7.52 g) of 1-bromo-2,4-difluorobenzene were loaded into a 100-ml flask, and the temperature of the 1-bromo-2,4-difluorobenzene was heated to 60°C. Next, 0.15 g of iron was added, and then 39 mmol (6.23 g) of bromine were dropped over 3 hours while the temperature of the mixture was kept at 60°C. After the completion of the dropping, the resultant was further subjected to a reaction at 60°C for 2 hours. After the temperature of the resultant reaction liquid had been cooled to room temperature, the reaction liquid was charged into a cold aqueous solution of sodium hydroxide, and the reaction product was extracted with hexane. An organic layer was washed with pure water and a saturated sodium chloride solution, and was dehydrated with anhydrous sodium sulfate. After that, the solvent was removed. The resultant residue was purified by means of silica gel chromatography (developing solvent: hexane), whereby 8.81 g of a compound A as colorless oil were obtained (84percent yield). |
83% | With bromine; iron In dichloromethane for 3 h; Reflux | 2,4-difluorobromobenzene (3 g, 15.5 mmol) and 260 mg of iron filings were placed in a two-neck flask, and 15 ml of dichloromethane was then added thereto. The two-neck flask was cooled in an ice bath, and a solution including bromine (1 ml, 18.7 mmol) and 15 ml of dichloromethane was added dropwise to the two-neck flask using an isobaric funnel. Next, the contents in the two-neck flask were heated under reflux for 3 hours. During heating, brown gas was produced. Then, the temperature was reduced to 20° C., and 50 ml of a sodium metabisulfite (Na2S2O5) aqueous solution (10percent) was mixed with the contents in the two-neck flask by stirring for 1 hour for terminating the reaction therein. Thereafter, the contents in the two-neck flask were washed several times with deionized water to collect an organic layer, the organic layer was dehydrated using sodium sulfate (Na2SO4), and the solvent in the organic layer was removed, followed by column chromatography (SiO2, n-hexane), thereby obtaining white crystals (3.5 g, 83percent yield). (0067) The spectrum analysis for the white crystals is: 1H NMR (400 MHz, CDCl3): δ 7.74 (t, J=7.6 Hz, 1H), 6.96 (t, J=8.0 Hz, 1H); 19F NMR (376 MHz, CDCl3, 298 K): δ −103.8 (dd, J=7.5 Hz, J=7.5 Hz). The white crystals were confirmed to be Compound L3-1 having a chemical structure represented by |
76% | With bromine; iron In 1,2-dichloro-ethane at 20℃; for 19 h; Inert atmosphere | Iron powder (16.49 g, 291 mmol) is added to 1-bromo-2,4-difluorobenzene (110 mL, 968 mmol) in 1,2-dichloroethane (968 mL) in a 3-neck flask at ambient temperature under a stream of nitrogen. A solution of bromine (59.7 mL, 1.16 mol) in 1,2-dichloroethane (968 mL) is added dropwise over 1 hour and the reaction mixture is stirred at ambient temperature for 18 h. The reaction mixture is cooled to 0° C. and a saturated aqueous solution of sodium bisulfate (1.11 L, 533 mmol) is added portionwise and the mixture is separated. The aqueous phase is extracted with dichloromethane. The organic layer is washed with a saturated aqueous solution of sodium bicarbonate, water, and brine. The organic layer is dried over sodium sulfate, and the solvent is removed under reduced pressure to give a residue purified with a pad of silica using diethyl ether to give the title compound (229 g, 76percent). 1H NMR (400 MHz, CDCl3) δ 7.70 (dd, J=4.6, 6.8 Hz, 1H), 6.95-6.92 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With butyl lithium In diethyl ether; hexane at -78℃; for 0.25 h; | A 1.6 M solution of butyl lithium in hexane (114 mL, 182 mmol) is added to a -78° C. solution of 1,5-dibromo-2,4-difluorobenzene (41.3 g, 152 mmol) in diethyl ether (290 mL). Dimethylformamide (14.4 g, 198 mmol) is added and the reaction is stirred at -78° C. for 15 minutes. The reaction is quenched with 1 N HCl (300 mL), is diluted with water, and extracted three times with ethyl acetate. The organic layer is dried over sodium sulfate and the solvent is removed under reduced pressure to give crude material that is purified by silica gel chromatography with a linear gradient of 0percent to 50percent CH2Cl2 in hexanes over 30 minutes to give the title compound (20.51 g, 61percent). GC-MS m/e (79Br/81Br) 220, 222 |
60% | Stage #1: With n-butyllithium In diethyl ether at -78℃; for 0.5 h; Stage #2: at -78℃; for 0.5 h; |
Preparation 145-bromo-2,4-difluorobenzaldehydeTo a solution of l,5-dibromo-2,4-difluorobenzene (17.5 g, 64.2 mmol) in ether (100 mL) at -78 °C was added n-BuLi (2.5 M solution, 30.8 mL, 77 mmol) over a period of 5 min, and the reaction mixture was stirred at -78 °C for 30 min. Then DMF (9.94 mL, 148 mmol) was added in one portion, and the mixture was stirred at -78 °C for 30 min. The reaction mixture was worked up with EtOAc/sat. NH4C1, and the crude product was purified by silica gel chromatography eluting with 0-10percent EtOAc/Hexanes to give the title compound as a slightly yellow oil (8.5 g, 60percent yield). XH NMR (400 MHz,CHLOROFORM-d) δ 10.26 (s, IH), 8.14 (t, J=7.5 Hz, IH), 7.05 (dd, J=9.8, 8.0 Hz, IH). |
60% | Stage #1: With n-butyllithium In diethyl ether at -78℃; for 0.583333 h; Stage #2: at -78℃; for 0.5 h; |
Preparation 2 5-bromo-2,4-difluorobenzaldehyde To a solution of l,5-dibromo-2,4-difluorobenzene (17.5 g, 64.2 mmol) in ether (100 mL) at -78 °C was added n-BuLi (2.5 M solution, 30.8 mL, 77 mmol) over a period of 5 min, and the reaction mixture was stirred at -78 °C for 30 min. Then DMF (9.94 mL, 148 mmol) was added in one portion, and the mixture was stirred at -78 °C for 30 min. The reaction mixture was worked up with EtOAc/sat. NH4C1, and the crude product was purified by silica gel chromatography eluting with 0-10percent EtOAc/Hexanes to give the title compound as a slightly yellow oil (8.5 g, 60percent yield). XH NMR (400 MHz, CHLOROFORM-d) δ 10.26 (s, 1H), 8.14 (t, J=7.5 Hz, 1H), 7.05 (dd, J=9.8, 8.0 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5 h; | To a solution of 1,5-dibromo-2, 4-difluorobenzene (Nucleosides, Nucleotides nucleic Acid, 201 (1 and2), 11-40 (2001) ) (8.8 g, 32.4 mmol) in diethylether (60 ml), 1.6 M n-BuLi in hexane (24.3 ml, 1.2 eq) was added at-78 C under N2 atmosphere. After stirring the reaction mixture at-78 C for 30 min, N-methyl-N- (methyloxy) acetamide (5.0 g, 1.5 eq) was dropped into to quench the reaction. The reaction mixture was stirred at the same temperature for further 30 min. After added acetic acid ( (5.2 ml), water (78 ml), the reaction mixture was extracted with diethylether. The obtained organic phase was washed by 0.2 N HCI aqueous, water, saturated NaHC03 aqueous and saturated NaCI aqueous, and dried over MgS04. After removing the solvent under reduced pressure, the residue was purified by Silica gel chromatography (n-Hexane/EtOAc = 49/1). Desired compound was obtained as pale yellow oil (4.94 g, 65percent). |
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