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CAS No. : | 162744-59-4 | MDL No. : | MFCD03094461 |
Formula : | C7H5BrF2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LSRHFWSNUFIKER-UHFFFAOYSA-N |
M.W : | 223.01 | Pubchem ID : | 2773303 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 40.19 |
TPSA : | 20.23 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.29 cm/s |
Log Po/w (iLOGP) : | 2.1 |
Log Po/w (XLOGP3) : | 1.93 |
Log Po/w (WLOGP) : | 2.91 |
Log Po/w (MLOGP) : | 3.15 |
Log Po/w (SILICOS-IT) : | 3.2 |
Consensus Log Po/w : | 2.66 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.78 |
Solubility : | 0.373 mg/ml ; 0.00167 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.98 |
Solubility : | 2.34 mg/ml ; 0.0105 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.65 |
Solubility : | 0.0505 mg/ml ; 0.000226 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.34 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
95.2% | With dimethylsulfide borane complex In tetrahydrofuran at 60℃; for 16 h; | To a solution of 4-bromo-2,6-difluorobenzoic acid (5 g, 21.10 mmol) in THF (100 mL) was added BH3. DMS (20.03 mL, 211 mmol) dropwise at rt. The resulting mixture was stirred at 60° C. for 16 h. After LCMS analysis showed the starting material had disappeared, the mixture was quenched by MeOH. The solvent was removed in vacuo to yield a white solid of (4-bromo-2,6-difluorophenyl)methanol (4.5 g, 20.02 mmol, 95.2percent yield), which was used in the next step without further purification: ES-LCMS m/z 222.1 (M+1). |
95.2% | With dimethylsulfide borane complex In tetrahydrofuran at 60℃; for 16 h; | To a solution of 4-bromo-2,6-difluorobenzoic acid (5 g, 21.10 mmol) in THF (100 mL) was added BH3 DMS (20.03 mL, 211 mmol) dropwise at rt. The resulting mixture was stirred at 60 °C for 16 h. After LCMS analysis showed the starting material had disappeared, the mixture was quenched by MeOH. The solvent was removed in vacuo to yield a white solid of (4-bromo-2,6- difluorophenyl)methanol (4.5 g, 20.02 mmol, 95.2percent yield), which was used in the next step without further purification: ES-LCMS m/z 222.1 (M+l). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | Stage #1: With sodium tetrahydroborate In methanol; dichloromethane at 0℃; for 1 h; Stage #2: With hydrogenchloride In methanol; dichloromethane; water for 0.5 h; |
To a stirred solution of 4-bromo-2,6-difluorobenzaldehyde (4.4 g, 19.9 mmol) in a 4: 1 mixture of CH2C12 and MeOH (100 mL) at 0 °C was added in one portion NaBH4 (829 mg, 21.9 mmol). The reaction mixture was stirred for 1 hour at 0 °C before being quenched by the careful addition of aqueous HC1 (1.0 M). After 30 min, the reaction was poured into water and extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2S04) and concentrated in vacuo to afford the title compound (4.24g, 95percent) as a white solid. MS (ISP): 223.2 ([{81Br}M-HD, 221.2 ([{79Br}M-HD. |
43.0 g | at 0℃; for 0.166667 h; | Step 1: Into a 1-L round-bottom flask, was placed a solution of 4-bromo-2,6- difluorobenzaldehyde (43.0 g, 195.45 mmol, 1.00 equiv) in methanol (500 mL) with stirring at 0 °C. Sodium borohydride (NaBH4 7.4 g, 195.45 mmol, 1.00 equiv) was then added in portions and the resulting mixture was stirred for 10 mm at 0 °C and then concentrated undervacuum. The residue was diluted with EtOAc, washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum to afford 43.0 g of(4-bromo-2,6- difluorophenyl)methanol as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With pyridine-SO3 complex; dimethyl sulfoxide; triethylamine In dichloromethane at 20℃; for 3 h; | Example A-14; 2-(4-bromo-2,6-difluorophenyl)-4-(4-methoxyphenyl)-1H-imidazole-5-carboxamide; Step a - 4-bromo-2,6-difluorobenzaldehyde; <n="84"/>To a solution of 4-bromo-2,6-difluorobenzylalcohol (0.20Og, 0.9mmol) in DCM (4ml) and DMSO (0.440ml) was added triethylamine (1 ml, 0.72mmol) and sulfur trioxide pyridine complex (0.57Og, 3.6mmol) and the resulting solution was stirred at room temperature for 3 hours. The solution was diluted with Et2O and washed with 0.5M aqueous HCI, 1M sodium bicarbonate solution and brine. The organic phase was dried over MgSO4 and the solvent removed in vacuo to afford 4-bromo-2,6-difluorobenzaldehyde (0.166g, 0.75mmol, 84percent) as a white solid. 1H NMR (CDCI3) δ 7.22 (2H, d), 10.29 (1 H, br. s). LCMS (2) Rt: 2.74min. |
76% | With manganese(IV) oxide In dichloromethane at 20℃; for 48 h; | 0.7 g (7.7 mmol 10 eq) of manganese dioxide is added to a solution of 1.0 g (0.77 mmol, 1 eq) of 2,6-difluoro-4-bromobenzylalcool in 15 mL of dichloromethane. The reaction medium is stirred at room temperature for 48 hours.The solid is filtered off and the solvent is evaporated off. The residual oil is chromatographed on silica gel (8/2 heptane/ethyl acetate) and 760 mg of 4-bromo-2,6-difluorobenzaldehyde are obtained. Yield = 76percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With hydrogen bromide In acetic acid at 20℃; for 1.5 h; | A solution of 5-Bromo-2-hydroxymethyl-1, 3-difluoro-benzene (0. 89g, 4.0 mmol) and 30 wtpercent of hydrogen bromide in acetic acid was stirred at room temperature for 90 minutes before it was poured into 80 ml of water. The mixture was extracted with pentane (3 X 50 ML) and the combined organic layers were washed with water (3 X 20 ML), dried over MGSO4 and concentrated at low pressure to afford the desired product (10.0 g, 98percent YIELD). 1H NMR (CDC13) 8 : 4.47 (s, 2H), 7.09-7. 10 (m, 1H), 7. 12-7. 13 (m, 1H). |
84% | With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 0 - 25℃; for 16.33 h; | A solution of 4-Bromo-2,6-difluorobenzyl alcohol (3.517 g, 15.77 mmol) and triphenylphosphine (4.55 g, 17.34 mmol) in dichloromethane (70 ml) was cooled to 0° C. and N-bromosuccinimide (3.086 g, 17.34 mmol) was added in 5 portions over 20 mins. The solution was warmed to 25° C. and stirred for 16 h. The reaction was quenched by the addition of dilute aqueous sodium bicarbonate. The resulting mixture was extracted with diethyl ether and the combined organic layers were washed with water, then brine and dried over sodium sulphate and concentrated under reduced pressure. The title compound was isolated by column chromatography on silica using 5 to 20percent ethyl acetate in n-pentane to give the title compound as an oil (3.785 g, 84percent).1H-NMR (400 MHz, CDCl3) δ: 7.10 (2H, m), 4.44 (2H, s); LC/MS Retention time 3.38 mins/M+H not observed. |
81% | With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 0 - 25℃; for 17.33 h; | A solution of 4-bromo-2,6-difluorobenzylalcohol (2.Og, 8.96mmol) and triphenylphosphine(2.59g, 9.89mmol) in dichloromethane (40ml) was cooled to O0C and N-bromosuccinimide(1.74g, 9.78mmol) was added in five portions over 20 minutes. The reaction mixture was warmed to 250C and stirred for 17hours. The reaction was quenched by the addition of dilute aqueous sodium hydrogen carbonate. The resulting mixture was extracted with diethyl ether and the combined organic layers were washed with water and saturated aqueous sodium chloride before being dried with sodium sulphate and concentrated under reduced pressure. The title compound was isolated by column chromatography on silica using 5 to 20percent ethyl acetate in n-pentane to give a dark oil (2.08g, 81percent).1H-NMR (400MHz, CDCI3): 4.44 (2H, s), 7.10 (2H, m). |
78% | Stage #1: With carbon tetrabromide In dichloromethane at 0℃; for 0.0833333 h; Stage #2: With triphenylphosphine In dichloromethane at 0 - 20℃; for 2 h; |
To a stirred solution of (4-bromo-2,6-difluoro-phenyl)methanol (4.2 g, 18.8 mmol) in CH2C12 (80 mL) at 0 °C was added CBr4 (7.81 g, 23.5 mmol). After 5 min, a solution of triphenylphosphine (6.17 g, 23.5 mmol) in CH2C12 (20 mL) was added dropwise and the resulting mixture was stirred at room temperature for 2 hours. The mixture was concentrated in vacuo and the residue was taken up in heptane (100 mL). The resulting precipitate (white solid) was collected through a sintered glass and washed with further heptane. The filtrate was concentrated in vacuo to afford the title compound (6.90g, 78percent) as a colorless oil which was used in the following step without further purification. |
61.2% | With phosphorus tribromide In dichloromethane at 0 - 20℃; | To a solution of (4-bromo-2,6-difluorophenyl)methanol (2 g, 8.97 mmol) in DCM (80 mL) was added tribromophosphine (2.91 g, 10.76 mmol) at 0° C. The resulting mixture was stirred at rt. After LCMS analysis showed the starting material had disappeared, the mixture was washed with aq NaHCO3 (40 mL) and brine (30 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified by silica column chromatography (PE/EA=5/1) to yield a colorless oil of 5-bromo-2-(bromomethyl)-1,3-difluorobenzene (1.6 g, 5.48 mmol, 61.2percent yield): 1H NMR (400 MHz, CD3OD) δ 7.12 (d, J=6.8 Hz, 2H), 4.47 (s, 2H). |
61.2% | With phosphorus tribromide In dichloromethane at 0 - 20℃; | To a solution of (4-bromo-2,6-difluorophenyl)methanol (2 g, 8.97 mmol) in DCM (80 inL) was added tribromophosphine (2.91 g, 10.76 mmol) at 0 °C. The resulting mixture was stirred at rt. After LCMS analysis showed the starting material had disappeared, the mixture was washed with aqueous NaHC03 (40 inL) and brine (30 mL). The organic layer was dried over NaaSOzi, filtered and concentrated. The crude material was purified by silica column chromatography (PE/EA = 5/1) to yield a colorless oil of 5-bromo-2-(bromomethyl)-l,3-difluorobenzene (1.6 g, 5.48 mmol, 61.2percent yield): lH NMR (400 MHz, CD3OD) δ 7.12 (d, J= 6.8 Hz, 2H), 4.47 (s, 2H). |
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