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CAS No. : | 59247-47-1 | MDL No. : | MFCD00093266 |
Formula : | C11H13BrO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BFJJYXUCGYOXDM-UHFFFAOYSA-N |
M.W : | 257.12 | Pubchem ID : | 11334366 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.36 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 59.88 |
TPSA : | 26.3 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) : | -5.42 cm/s |
Log Po/w (iLOGP) : | 2.99 |
Log Po/w (XLOGP3) : | 3.45 |
Log Po/w (WLOGP) : | 3.4 |
Log Po/w (MLOGP) : | 3.53 |
Log Po/w (SILICOS-IT) : | 3.11 |
Consensus Log Po/w : | 3.3 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.73 |
Solubility : | 0.0482 mg/ml ; 0.000188 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.68 |
Solubility : | 0.0533 mg/ml ; 0.000207 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.15 |
Solubility : | 0.0181 mg/ml ; 0.0000703 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 1.6 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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% | at -78 - 20℃; for 2 h; | tert-Butyl 4-bromobenzoate. To a solution of 4-bromobenzoyl chloride (25.08 g, 114 mmol) in THF (120 mL) at -78°C was added potassium toert-butoxide (120 mL, 1 M in THF, 120 mmol). The reaction mixture was warmed from -78°C to room temperature over 2 h, and diluted with diethyl ether. The organic phase was washed with saturated NaHCψ3 (2 x), brine (1 x), dried over MgSO4, filtered, and EPO <DP n="74"/>concentrated. Purification by flash column chromatography on silica gel (5percent ethyl acetate in hexanes) gave tert-butyl 4-bromobenzoate (27.96 g, 95percent) as a colorless oil: 1H NMR (600 MHz, CDCl3) δ 7.84 (d, J = 8.5 Hz, 2H), 7.54 (d, J = 8.5 Hz, 2H), 1.59 (s, 9H); ESIMS calcd 257.0 (M+ + H), found 257.1 (M+ + H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With dmap In <i>tert</i>-butyl alcohol at 20℃; for 12 h; | Tert-butyl 4-bromobenzoate. To a solution of 4-dimethylamiopryidine (1.5 g, 12.5 mmol) in tert-butanol (20 mL) were added 4-bromobenzoic acid (5 g, 25 mmol) and di-tert-butyl dicarbonate (10.95 g, 0.05 mol). The mixture was stirred at 20°C for 12 hours. The resultant mixture was concentrated in vacuo to give a residue and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 30: 1) to give tert-butyl 4- bromobenzoate (4 g, 62percent>). |
62% | With dmap In <i>tert</i>-butyl alcohol at 20℃; for 12 h; | To a solution of 4-dimethylamiopryidine (1.5 g, 12.5 mmol) in tert-butanol (20 mL) were added 4-bromobenzoic acid (5 g, 25 mmol) and di-tert-butyl dicarbonate (10.95 g, 0.05 mol). The mixture was stirred at 20° C. for 12 hours. The resultant mixture was concentrated in vacuo to give a residue and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=30:1) to give tert-butyl 4-bromobenzoate (4 g, 62percent). |
21% | With dmap In <i>tert</i>-butyl alcohol at 50℃; | To a 1000-mL round-bottom flask was added 4-bromobenzoic acid 52a (20 g, 99.495 mmol, 1.0 equiv.), tert-butano (200 mL), 4-dimethylaminopyridine (1.22 g, 9.99 mmol, 0.10equiv.), and Boc20 (32 7 g, 149.83 mmoL 150 equiv) and the resulting mixture ·was stirredat 50 °C ovemight. The mixture was diluted vvith 200 mL of H20 and extracted with ethylacetate (300 mL x 2). "fl1e combined organic extracts were washed with brine (300 mL x 2),dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. Thel 0 crude product was purified by Flash-Prep-HPLC using the following conditions: Column,silica gel; mobile phase, PE:EA = 100:0 increasing to 90:10 over 5 min; Detector, UV 254nm, to provide 5.43 g (21 percent) oftert-butyl4-bromobenzoate 52b as a colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | at 20℃; for 12 h; | tert-Butyl 4-bromobenzoate. To a solution of 4-dimethylaminopyridine (1.5 g, 12.5 mmol) in tert-butanol(20 mL) were added 4-bromobenzoic acid (5.0 g, 25 mmol) and di-tert-butyldicarbonate (10.95 g, 50 mmol). The mixture was stirred at 20 °C for 12 h. The resultant mixture was concentrated in vacuo and the residue was purified by silica gel chromatography (petroleumether/ethyl acetate = 30:1) to provide tert-butyl 4-bromobenzoate (4.0 g, 62percent). |
55% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 20℃; for 18 h; | To a solution of 4-bromobenzoic acid (lOg, 49.7 mmol) in Chlorofonri (150 ml), 2- methylpropan-2-ol (18.44g, 249 mmol), EDC.HC1 (23.84g, 124 mmol), followed by DMAP (15.19g, 124 mmol) was added and stined for 18h at room temperature. After completion of reaction as indicated by TLC, the mixture was poured into water and extracted with DCM. The organic layer was collected and dried over sodium sulphate,finally evaporated and purified by column chromatography (7g, 55 percent). 1H NMR (400MHz, Chloroform-d) 7.87 (d, 2H), 7.57 (d, 2H), 1.61 (s, 9H). |
49 g | With dmap; diisopropyl-carbodiimide In dichloromethane at 35℃; for 5 h; | In dichloromethane, 4-bromobenzoic acid (50 g), tert-butyl alcohol (20.3 g), and dimethylaminopyridine (12.2 g) were dissolved. The resulting solution was added drop- wise to diisopropylcarbodiimide (DIC, 37.7 g) at 35° C. The resulting mixture was stirred for 5 hours. Subsequently, the reaction liquid was filtered, and the filtrate was concentrated. The resulting solid was purified by column chromatography. Hereby, the compound M- 1 (49 g) was prepared |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With 1H-imidazole; tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In water at 80℃; for 7 h; Green chemistry | General procedure: To a mixture of benzyl alcohol (108 mg, 1.0 mmol) and TBHP(180 mg, 2.0 mmol) in water (3 ml), the catalyst TBAI (73.8 mg,0.2 mmol), imidazole (136 mg, 2.0 mmol), and MeOH (2 ml)were added, and the mixture was stirred at 80 °C for 8 h. Theprogress of the reaction was monitored by TLC. After completionof reaction, the reaction mixture was cooled to room temperature.Then MeOH was distilled out, and the organic productwas extracted with ethyl acetate (3 × 10 ml), repeatedly washedwith distilled water (4 × 5 ml) to remove the unreacted TBHP,dried with anhydrous sodium sulfate, and the solvent was evaporatedunder reduced pressure to afford methyl benzoate (112mg, yield 82percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With 3-chloro-benzenecarboperoxoic acid; copper(ll) bromide In 1,4-dioxane at 70℃; for 3 h; | General procedure: To a solution of m-CPBA(1.2 mmol) and CuBr2 (0.1 mmol) in dry 1,4-dioxane (10 mL) was addeddropwise a solution of compound 1 (1mmol). The reaction mixture was stirred at the designated temperature until theTLC indicated the consumption of the starting martial compound 1. After the reaction was completed,the reaction mixture was allowed to cool to room temperature, and EtOAc (20 mL)was added. The resulting mixture was washed with saturated aqueous Na2S2O3(10mL) and saturated aqueousNa2CO3 (10 mL). The organic layer was dried overanhydrous Na2SO4, filtered, and removed under reducedpressure. The residue was purified by flash column chromatography on silica gelto give the desired products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With pyridine In dichloromethane | A. tert.-Butyl 4-Bromobenzoate To a mixture of 5.5 g of dry tert.-butanol and 7.08 g of dry pyridine is added a solution of 9.79 g of 4-bromobenzoyl chloride in 20 ml of anhydrous methylene chloride. The mixture is stirred under nitrogen for 2 days. The reaction mixture is then diluted with methylene chloride, and the organic solution extracted with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residual oil is distilled under reduced pressure to give 8.9 g (70percent) of tert.-butyl 4-bromobenzoate as a colorless oil: b.p. 91°-92° C./1.2 mm; NMR (CDCl3, 80 MHz) delta 1.59 (s, 9H), 7.53 (d, 2H, J=8.7 Hz); IR (neat) 2970, 1710, 1585, 1475, 1390, 1290, 1160, 1110, 1070, 845 and 745 cm-1. Anal. Calcd. for C11 H13 BrO2: C, 51.38; H, 5.09; Br, 31.08. Found: C, 51.41; H, 5.36; Br, 30.38. |
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