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CAS No. : | 695-96-5 | MDL No. : | MFCD00002319 |
Formula : | C6H4BrClO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZIYRDJLAJYTELF-UHFFFAOYSA-N |
M.W : | 207.45 | Pubchem ID : | 69670 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 41.18 |
TPSA : | 20.23 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) : | -5.32 cm/s |
Log Po/w (iLOGP) : | 2.1 |
Log Po/w (XLOGP3) : | 3.16 |
Log Po/w (WLOGP) : | 2.81 |
Log Po/w (MLOGP) : | 2.84 |
Log Po/w (SILICOS-IT) : | 2.7 |
Consensus Log Po/w : | 2.72 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.61 |
Solubility : | 0.0509 mg/ml ; 0.000245 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.26 |
Solubility : | 0.115 mg/ml ; 0.000556 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.3 |
Solubility : | 0.105 mg/ml ; 0.000506 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.4 |
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 |
---|---|---|
58% | With tris(2,2'-bipyridyl)ruthenium dichloride; carbon tetrabromide In acetonitrile at 20℃; Irradiation | General procedure: To a 10 mL round bottom flask equipped with a magnetic stir bar were added phenols or alkenes (0.1 mmol), CBr4 (33 mg, 0.1 mmol), dry CH3CN (1 mL) and Ru(bpy)3Cl2 (3.8 mg, 0.005 mmol). The mixture was irradiated with blue LEDs (1 W) at room temperature open to air until the starting material disappeared completely (monitored by TLC). After the reaction was completed, the solvent was concentrated in vacuo. The residue was purified by flash column chromatography to give the final product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With o-xylylene bis(triethylammonium tribromide) In acetonitrile at 20℃; for 0.0833333 h; | General procedure: To a magnetic solution of aromatic compound (1 mmol)in acetonitrile (5 mL), OXBTEATB (0.233 g, 0.5 mmol) wasadded and stirred at room temperature for the appropriatetime (Table 1). The reaction was monitored by TLC (eluent:n-hexane/ethyl acetate: 5/1). The reaction mixture was transferredinto a separatory funnel after filtration of OXBTEABand was extracted with water (15 mL) and dichloromethane(20 mL). The organic layer was dried over anhydrousNa2SO4, and the solvent was concentrated in a rotary evaporator.The crude product was purified by passing it over acolumn of silica gel using a mixture of n-hexane and ethylacetate as the eluent. In order to regenerate the reagent, whitesolid was treated with liquid bromine. All the product structureswere confirmed by comparison of melting point or 1HNMR spectra with ones reported in the literature [29a-29e]. |
68% | With potassium hydrogensulfate; isoquinolinium dichromate; potassium bromide In water at 20℃; Sonication | General procedure: The general method for ultrasonically assisted brominationreaction is almost similar to conventional reaction as mentionedabove. A centimolar (0.01 mol) organic substrate (phenols,anilines, or acetanilides), 0.001 mol potassium halide(KBr), about 50 mg of dilute KHSO4, and hypervalent Cr(VI) reagent (IQCC or IQDC) were suspended in about30 mL solvent (DCE or ACN) in a previously cleaned roundbottom(R.B) flask placed in a sonicator. The reaction mixtureis sonicated at room temperature about 30–40 min. Progressof the reaction was monitored by TLC technique. Workupprocedure after completion of the reaction mixture is similarto the one described previously. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sodium nitrate; sulfuric acid; acetic acid In water at 25 - 30℃; Large scale | The reaction flask was successively added with acetic acid (7.5 L) 4-chloro-2-bromophenol (1500.0 g, 7.2 mol) was stirred well;Sodium nitrate was added dropwise at room temperature(1229.0 g, 14.5 mol)And concentrated sulfuric acid(1418.0 g, 14.5 mol) in water (1.4 L);After the drop, the temperature control 25-30°C reaction about 20-30min;The reaction was stopped and poured into ice water (7.5 L) and stirred for 20 min.The filter cake was washed with water until the filtrate was near neutral (pH 6-7). The filter cake was dried to obtain a yellow solid: 1742 g, yield: 95percent. |
80.1% | With nitric acid In water; acetic acid | (a) 2-bromo-4-chloro-6-nitro-phenol A solution of 2-bromo-4-chloro-phenol (99.24 g, 480 mmol) in acetic acid (110 ml) and acetic anhydride (125 ml) was cooled to -10°C. Within 1 hour a solution containing 100percent nitric acid (33 ml) and acetic acid (40 ml) was added between -10° and -5°C, with stirring. The mixture was stirred for an additional 1.5 hours at 0-5 °C, then the suspension poured onto 300 g of ice in 700 ml of water and stirred for a further 0.5 hour. The solid was collected, washed, and dried to give 97.12 g (80.1percent) of the title compound (mp 121-2°C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With sodium hydroxide In dichloromethane; water at 20℃; for 22 h; | 2-Bromo-4-chloro-1-methoxybenzene (47). A solution of sodium hydroxide (836 mg, 20.9 mmol) in water (8.0 mL) was added to a solution of 2-bromo-4-chlorophenol (45) (2.1 g, 9.92 mmol) and tetrabutylammonium bromide (336.4 mg, 1.03 mmol) in dichloromethane. Dimethyl sulfate (1.5 mL, 15.69 mmol) was added. The resulting mixture was stirred at room temperature for 22 h and then 1 N aq HCl (about 2 mL) was added to quench the reaction. The organic phase was separated and the aqueous phase was extracted with dichloromethane (2.x.15 mL). The combined organic phase was washed with brine, dried over sodium sulfate and concentrated to afford an oil. The crude product was purified by column chromatography on silica gel (10 g) using EtOAc-hexanes (5percent) to afford the product 47 as a colorless oil (2.17 g) in 99percent yield. See, Dischino, D. D.; Gribkoff, V. K.; Hewawasam, P.; Luke, G. M.; Rinehart, J. K.; Spears, T. L.; Starrett Jr, J. E. Synthesis of 3H and 14 C Labeled (S)-3-(5-Chloro-2-methoxyphenyl)-1,3-dihydro-3-fluoro-6-(trifluoromethyl)-2H-indol-2-one, Maxipost.(TM).. An Agent for Post-Stroke Neuroprotection. J. Label. Compd. Radiopharm. 2003, 46, 139-149, the disclosure of which is incorporated herein by reference. 1H NMR (300 MHz, CDCl3) δ 7.51 (d, J=2.4 Hz, 1H), 7.22 (dd, J=2.4 Hz, J=8.7 Hz, 1H), 6.80 (d, J=8.7 Hz, 1H), 3.86 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With potassium carbonate In acetone for 6 h; Reflux | General procedure: To a stirred solution of 7aa (19.11 g, 0.10 mol) or 7ab (20.75 g, 0.10 mol) in acetone (150 mL) was added K2CO3 (13.80 g, 0.10 mol) and MeI (12.61, 0.10 mol) at room temperature. After the mixture being refluxed for 6 h, the solvent was evaporated under reduced pressure and the residue was poured into H2O (150 mL) and extracted with CH2Cl2 (2 .x. 100 mL). The combined organic layer was washed with H2O (2 .x. 100 mL) and dried with anhydrous NaSO4. The solvent was evaporated to afford light yellow oil 8aa (94percent) or 8ab (96percent). |
98% | With potassium carbonate In water; acetone | EXAMPLE 109 9-Chloro-1,2-dihydro-2,2,4-trimethyl-5-coumarino[3,4-f]quinoline (Compound 209, structure 41 of Scheme XI, where R1 =H, R2 =Cl) 2-Bromo-4-chloroanisole (structure 36 of Scheme XI, where R1 =H, R2 =Cl) In a 250 mL r.b. flask, a solution of 2-bromo-4-chlorophenol (Lancaster: 16.94 g, 81.6 mmol, 1.0 equivuiv) in acetone (160 mL) was treated sequivuentially with iodomethane (6.10 mL, 98 mmol, 1.2 equivuiv), potassium carbonate (12 g), and water (4 mL). The reaction mixture was heated at reflux for 3 h, cooled to rt, and the bulk of the volatiles was removed under reduced pressure. The residue was poured into water (140 mL) and extracted with EtOAc (3*150 mL). The extracts were washed with brine (1*100 mL), combined, dried (K2 CO3), filtered through a pad of Celite.(TM)., and concentrated to a clear oil. Short-path distillation (80°-85° C., 1 Torr) afforded 17.74 g (98percent) of 2-bromo-4-chloroanisole as a clear liquid. Data for 2-bromo-4-chloroanisole: 1 H NMR (400 MHz, acetone-d6) 7.53 (d, J=2.5, 1H); 7.24 (dd, J=9.7, 2.5, 1H); 6.81 (d, J=9.7, 1H); 3.88 (s, 3H). |
98% | With potassium carbonate In water; acetone | EXAMPLE 109 9-Chloro-1,2-dihydro-2,2,4-trimethyl-5-coumarino[3,4-f]quinoline (Compound 209, structure 41 of Scheme XI, where R1 =H, R2 =Cl) 2-Bromo-4-chloroanisole (structure 36 of Scheme XI, where R1 =H, R2 =Cl) In a 250 mL r.b. flask, a solution of 2-bromo-4-chlorophenol (Lancaster: 16.94 g, 81.6 mmol, 1.0 equivuiv) in acetone (160 mL) was treated sequivuentially with iodomethane (6.10 mL, 98 mmol, 1.2 equivuiv), potassium carbonate (12 g), and water (4 mL). The reaction mixture was heated at reflux for 3 h, cooled to rt, and the bulk of the volatiles was removed under reduced pressure. The residue was poured into water (140 mL) and extracted with EtOAc (3*150 mL). The extracts were washed with brine (1*100 mL), combined, dried (K2 CO3), filtered through a pad of Celite.(TM)., and concentrated to a clear oil. Short-path distillation (80°-85° C., 1 Torr) afforded 17.74 g (98percent) of 2-bromo-4-chloroanisole as a clear liquid. Data for 2-bromo-4-chloroanisole: 1 H NMR (400 MHz, acetone-d6) 7.53 (d, J=2.5, 1 H); 7.24 (dd, J=9.7, 2.5, 1 H); 6.81 (d, J=9.7, 1 H); 3.88 (s, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With potassium carbonate In water; acetone | EXAMPLE 109 9-Chloro-1,2-dihydro-2,2,4-trimethyl-5-coumarino[3,4-f]quinoline (Compound 209, structure 41 of Scheme XI, where R1 =H, R2 =Cl) 2-Bromo-4-chloroanisole (structure 36 of Scheme XI, where R1 =H, R2 =Cl) In a 250 mL r.b. flask, a solution of 2-bromo-4-chlorophenol (Lancaster: 16.94 g, 81.6 mmol, 1.0 equivuiv) in acetone (160 mL) was treated sequivuentially with iodomethane (6.10 mL, 98 mmol, 1.2 equivuiv), potassium carbonate (12 g), and water (4 mL). The reaction mixture was heated at reflux for 3 h, cooled to rt, and the bulk of the volatiles was removed under reduced pressure. The residue was poured into water (140 mL) and extracted with EtOAc (3*150 mL). The extracts were washed with brine (1*100 mL), combined, dried (K2 CO3), filtered through a pad of Celite.(TM)., and concentrated to a clear oil. Short-path distillation (80°-85° C., 1 Torr) afforded 17.74 g (98percent) of 2-bromo-4-chloroanisole as a clear liquid. Data for 2-bromo-4-chloroanisole: 1 H NMR (400 MHz, acetone-d6) 7.53 (d, J=2.5, 1H); 7.24 (dd, J=9.7, 2.5, 1H); 6.81 (d, J=9.7, 1H); 3.88 (s, 3H). |
98% | With potassium carbonate In water; acetone | EXAMPLE 109 9-Chloro-1,2-dihydro-2,2,4-trimethyl-5-coumarino[3,4-f]quinoline (Compound 209, structure 41 of Scheme XI, where R1 =H, R2 =Cl) 2-Bromo-4-chloroanisole (structure 36 of Scheme XI, where R1 =H, R2 =Cl) In a 250 mL r.b. flask, a solution of 2-bromo-4-chlorophenol (Lancaster: 16.94 g, 81.6 mmol, 1.0 equivuiv) in acetone (160 mL) was treated sequivuentially with iodomethane (6.10 mL, 98 mmol, 1.2 equivuiv), potassium carbonate (12 g), and water (4 mL). The reaction mixture was heated at reflux for 3 h, cooled to rt, and the bulk of the volatiles was removed under reduced pressure. The residue was poured into water (140 mL) and extracted with EtOAc (3*150 mL). The extracts were washed with brine (1*100 mL), combined, dried (K2 CO3), filtered through a pad of Celite.(TM)., and concentrated to a clear oil. Short-path distillation (80°-85° C., 1 Torr) afforded 17.74 g (98percent) of 2-bromo-4-chloroanisole as a clear liquid. Data for 2-bromo-4-chloroanisole: 1 H NMR (400 MHz, acetone-d6) 7.53 (d, J=2.5, 1 H); 7.24 (dd, J=9.7, 2.5, 1 H); 6.81 (d, J=9.7, 1 H); 3.88 (s, 3 H). |
98% | With potassium carbonate In water; acetone | EXAMPLE 109 9-Chloro-1,2-dihydro-2,2,4-trimethyl-5-coumarino[3,4-f]quinoline (Compound 209, structure 41 of Scheme XI, where R1 =H, R2 =Cl) 2-Bromo-4-chloroanisole (structure 36 of Scheme XI, where R1 =H, R2 =Cl) In a 250 mL r.b. flask, a solution of 2-bromo-4-chlorophenol (Lancaster: 16.94 g, 81.6 mmol, 1.0 equivuiv) in acetone (160 mL) was treated sequivuentially with iodomethane (6.10 mL, 98 mmol, 1.2 equivuiv), potassium carbonate (12 g), and water (4 mL). The reaction mixture was heated at reflux for 3 h, cooled to rt, and the bulk of the volatiles was removed under reduced pressure. The residue was poured into water (140 mL) and extracted with EtOAc (3*150 mL). The extracts were washed with brine (1*100 mL), combined, dried (K2 CO3), filtered through a pad of Celite.(TM)., and concentrated to a clear oil. Short-path distillation (80°-85° C., 1 Torr) afforded 17.74 g (98percent) of 2-bromo-4-chloroanisole as a clear liquid. Data for 2-bromo-4-chloroanisole: 1 H NMR (400 MHz, acetone-d6) 7.53 (d, J=2.5, 1H); 7.24 (dd, J=9.7, 2.5, 1H); 6.81 (d, J=9.7, 1H); 3.88 (s, 3H). |
98% | With potassium carbonate In water; acetone | EXAMPLE 109 9-Chloro-1,2-dihydro-2,2,4-trimethyl-5-coumarino[3,4-f]quinoline (Compound 209, structure 41 of Scheme XI, where R1 =H, R2 =Cl) 2-Bromo-4-chloroanisole (structure 36 of Scheme XI, where R1 =H, R2 =Cl) In a 250 mL r.b. flask, a solution of 2-bromo-4-chlorophenol (Lancaster: 16.94 g, 81.6 mmol, 1.0 equivuiv) in acetone (160 mL) was treated sequivuentially with iodomethane (6.10 mL, 98 mmol, 1.2 equivuiv), potassium carbonate (12 g), and water (4 mL). The reaction mixture was heated at reflux for 3 h, cooled to rt, and the bulk of the volatiles was removed under reduced pressure. The residue was poured into water (140 mL) and extracted with EtOAc (3*150 mL). The extracts were washed with brine (1*100 mL), combined, dried (K2 CO3), filtered through a pad of Celite.(TM)., and concentrated to a clear oil. Short-path distillation (80°-85° C., 1 Torr) afforded 17.74 g (98percent) of 2-bromo-4-chloroanisole as a clear liquid. Data for 2-bromo-4-chloroanisole: 1 H NMR (400 MHz, acetone-d6) 7.53 (d, J=2.5, 1H); 7.24 (dd, J=9.7, 2.5, 1H); 6.81 (d, J =9.7, 1H); 3.88 (s, 3H). |
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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