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CAS No. : | 1214348-81-8 | MDL No. : | MFCD11847190 |
Formula : | C7H4BrClF2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XFRGUUPMGQRCGB-UHFFFAOYSA-N |
M.W : | 257.46 | Pubchem ID : | 46311537 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 45.75 |
TPSA : | 9.23 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.92 cm/s |
Log Po/w (iLOGP) : | 2.33 |
Log Po/w (XLOGP3) : | 4.16 |
Log Po/w (WLOGP) : | 4.54 |
Log Po/w (MLOGP) : | 3.44 |
Log Po/w (SILICOS-IT) : | 3.57 |
Consensus Log Po/w : | 3.61 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.3 |
Solubility : | 0.0131 mg/ml ; 0.0000507 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.06 |
Solubility : | 0.0223 mg/ml ; 0.0000867 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -4.22 |
Solubility : | 0.0156 mg/ml ; 0.0000607 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.78 |
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 |
---|---|---|
98% | With caesium carbonate In water; N,N-dimethyl-formamide at 100℃; for 4 h; | To a solution of 2-bromo-4-chlorophenol (1 g, 4.8 mmol) in DMF/water (45 mL/5 mL) was added sodium chlorodifluoroacetate (1.95 g, 12.0 mmol) and cesium carbonate (3.14 g, 9.64 mmol), and the reaction mixture was heated to 100° C. for 4 hours. The reaction mixture was cooled and diluted with TBME (20 mL) and water (20 mL). The organic layer was collected, washed with saturated aqueous NaHCO3 solution, brine, dried over Na2SO4 and concentrated in vacuo to afford the title compound (1.21 g, 98percent). 1HNMR (400 MHz, CDCl3): δ ppm 6.52 (m, 1H), 7.18 (t, 1H), 7.31 (m, 1H), 7.64 (d, 1H). |
48% | With caesium carbonate In water; N,N-dimethyl-formamide at 100℃; for 16 h; | To a solution of 2-bromo-4-chlorophenol (4.98 g, 24.0 mmol) in DMF (25 mL) was added sodium chlorodifluoroacetate (8.42 g, 55.2 mmol), cesium carbonate (10.97 g, 33.67 mmol) and water (2.5 mL). The reaction was stirred at 100° C. for 16 hours. The reaction mixture was partitioned between ethyl acetate and water, the organic portion washed with brine, dried (MgSO4), and evaporated. The crude product was purified by flash chromatography on silica eluting with 0-20percent EtOAc in heptanes to yield 2-bromo-4-chloro-1-(difluoromethoxy)benzene as a clear, colorless oil (2.98 g, 48percent). LCMS (ESI) no m/z signal; 1H NMR (400 MHz, DMSO-d6) δ: (ppm) 7.90 (d, 1H), 7.54 (dd, 1H), 7.38 (d, 1H), 7.28 (t, 1H). |
48% | With caesium carbonate In water; N,N-dimethyl-formamide at 100℃; for 16 h; | To a solution of 2-bromo-4-chlorophenol (4.98 g, 24.0 mmol) in DMF (25 mL) was added sodium chlorodifluoroacetate (8.42 g, 55.2 mmol), cesium carbonate (10.97 g, 33.67 mmol) and water (2.5 mL). The reaction was stirred at 100 °C for 16 hours. The reaction mixture was partitioned between ethyl acetate and water, the organic portion washed with brine, dried (MgS04), and evaporated. The crude product was purified by flash chromatography on silica eluting with 0-20percent EtOAc in heptanes to yield 2-bromo- 4-chloro-l-(difluoromethoxy)benzene (2.98 g, 48percent) as a clear, colorless oil. LCMS (ESI) no m/z signal; 1H NMR (400 MHz, DMSO-^): δ 7.90 (d, 1H), 7.54 (dd, 1H), 7.38 (d, 1H), 7.28 (t, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium hydroxide In water; acetonitrile for 0.0833333 h; Cooling with ice | [1555] 36 ml of aqueous potassium hydroxide solution(6M) were added to a solution of 3.5 g (16.9 mmol) of2-bromo-4-chlorophenol in 36 ml of acetonitrile, the mixturewas cooled in an ice bath and 6.5 ml (26.9 mmol, 1.6 eq.) ofdifluoromethyl trifluormethanesulphonate [Angew. Chern.Int. Ed. 2013, 52, 1-5; Journal of Fluorine Chemistry 2009,130, 667-670] were added dropwise with vigorous stirring.The reaction mixture was stirred for 5 min and diluted with200 ml of water. The aqueous phase was extracted twice within each case 150 ml of diethyl ether. The combined organicphases were dried (sodium sulphate), filtered, concentratedunder reduced pressure and dried. The aqueous phase wasonce more extracted with diethyl ether. The organic phasewas dried (sodium sulphate), filtered, concentrated underreduced pressure and dried. Yield of the two combined residues:3.4 g (80percent of theory)[1556] LC/MS [Method 9]: R,=3.51 min; MS (ESipos):m/z=256 (M+Ht[1557] 1H-NMR (400 MHz, DMSO-d6): o [ppm]=7.91 (d,lH), 7.55 (dd, lH), 7.37 (d, lH), 7.30 (t, lH). |
80% | With potassium hydroxide In water; acetonitrile for 0.0833333 h; Cooling with ice | 36 ml of aqueous potassium hydroxide solution (6M) were added to a solution of 3.5 g (16.9 mmol) of 2-bromo-4-chlorophenol in 36 ml of acetonitrile, the mixture was cooled in an ice bath and 6.5 ml (26.9 mmol, 1.6 eq.) of difluoromethyl trifluormethanesulphonate [Angew. Chem. mt. Ed. 2013, 52, 1-5; Journal of Fluorine Chemistry 2009, 130, 667-670] were added dropwise with vigorous stirring. The reaction mixture was stirred for 5 mm and diluted with 200 ml of watet The aqueous phase was extracted twice with in each case 150 ml of diethyl ethet The combined organic phases were dried (sodium sulphate), filtered, concentrated under reduced pressure and dried. The aqueous phase was once more extracted with diethyl ethet The organic phase was dried (sodium sulphate), filtered, concentrated under reduced pressure and dried. Yield of the two combined residues: 3.4 g (80percent of theory)10654] LC/MS [Method 9]: R=3.51 mm; MS (ESIpos):mlz=256 (M+H), 10655] ‘H-NMR (400 MHz, DMSO-d5): ö [ppm]=7.91 (d, 1H), 7.55 (dd, 1H), 7.37 (d, 1H), 7.30 (t, 1H). |
3.4 g | With potassium hydroxide In water; acetonitrile for 0.0833333 h; Cooling with ice | 36 ml of aqueous potassiumhydroxide solution (6M) were added to a solution of 3.5 g (16.9 mmol) of2-bromo-4-chlorophenol in 36 ml of acetonitrile, the mixture was cooled in anice bath and 6.5 ml (26.9 mmol, 1.6 eq.) of difluoromethyl trifluormethanesulphonate were added dropwise with vigorous stirring. The reaction mixture was stirredfor 5 min and diluted with 200 ml of water. The aqueous phase was extractedtwice with in each case 150 ml of diethyl ether. The combined organic phaseswere dried (sodium sulphate), filtered, concentrated under reduced pressure anddried. The aqueous phase was once more extracted with diethyl ether. Theorganic phase was dried (sodium sulphate), filtered, concentrated under reducedpressure and dried. Yield of the two combined residues: 3.4 g (80percent of theory) |
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