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CAS No. : | 94278-68-9 | MDL No. : | MFCD04115925 |
Formula : | C8H7BrF2O | Boiling Point : | 210.4°C at 760 mmHg |
Linear Structure Formula : | - | InChI Key : | N/A |
M.W : | 237.04 g/mol | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 45.69 |
TPSA : | 9.23 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.86 cm/s |
Log Po/w (iLOGP) : | 2.52 |
Log Po/w (XLOGP3) : | 2.65 |
Log Po/w (WLOGP) : | 3.56 |
Log Po/w (MLOGP) : | 3.44 |
Log Po/w (SILICOS-IT) : | 3.67 |
Consensus Log Po/w : | 3.17 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.22 |
Solubility : | 0.144 mg/ml ; 0.000607 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.49 |
Solubility : | 0.758 mg/ml ; 0.0032 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.35 |
Solubility : | 0.0107 mg/ml ; 0.000045 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.78 |
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | 3261 |
Hazard Statements: | H314 | Packing Group: | Ⅱ |
GHS Pictogram: |
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* 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 |
---|---|---|
66% | With phosphorus(V) oxybromide In tetrahydrofuran at 20℃; for 2h; | 56.3 Step3: Step3: To a cold stirring solution of (2,6-difluoro-4-methoxyphenyl)MeOH (0.5 g, 2.87 mmol, 1 eq) in THF (20 ml) was portion wise added ROB FontWeight="Bold" FontSize="10" (1.65 g, 5.74 mmol, 2 eq). The reaction mixture then stirred for 2 h at RT. The reaction mixture was quenched by saturated NaHCCb solution under cooling conditions. The organic layer was separated and aqueous layer was extracted by EtOAc (50 ml). The combined organic layer was washed by water (30 ml) and brine (30 ml). [71] The organic layer was dried over anhydrous Na2SC>4, concentrated under reduced pressure to get the crude material which was purified by silica gel (230-400 mesh silica gel; 10% EtO Ac/hexane; R value-0.5) to afford 2-(bromomethyl)-1,3-difluoro-5-methoxybenzene (0.45 g, 66%) as color less liquid. |
With hydrogen bromide; acetic acid for 0.75h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | In water; N,N-dimethyl-formamide at 20℃; for 0.5h; | 56.4 Step4: Step4: To a cold stirring solution of 2-(bromomethyl)-l,3-difluoro-5-methoxybenzene (9.5 g, 40.08 mmol, 1 eq) in DMF (38 ml) was slowly added a solution of KCN (3.23 g, 49.7 mmol, 1.24 eq) in water (7.34 ml). The reaction mixture then stirred for 30 min at RT. Water (48 ml) and NaHCCb solution (48 ml) were added to the reaction mixture. The reaction mixture was then extracted by Et20 (2 x 200 ml). The combined organic layer was washed by water (4 x 80 ml) followed by brine (200 ml). The organic layer was dried over anhydrous Na2SC>4, concentrated under reduced pressure to get the crude material, which was purified by silica gel (230-400 mesh silica gel; 10% EtOAc/hexane; Rvalue-0.4) to afford 2-(2,6-difluoro-4-methoxyphenyl)acetonitrile (3.5 g, 48%) as color less liquid. |
In water; N,N-dimethyl-formamide Cooling with water bath; | 3.A Step A: Preparation of 2,6-Difluoro-4-methoxybenzeneacetonitrileA solution of KCN (0.88 g, 13 mmol) dissolved in water (2 mL) was added dropwise to a water-bath-cooled solution of 2,6-difluoro-4-methoxybenzyl bromide (2.50 g, 10.5 mmol) in Λ/,Λ/-dimethylformamide (10 mL). The reaction mixture was stirred for 20 min. Water was added (20 mL) and then the reaction mixture was poured into saturated aqueous NaΗCC>;3 solution (20 mL) and extracted with ether (50 mL). The organic phase was washed with water (5 x 25 mL), dried over MgSOφ and concentrated to give an oil, which crystallized on standing to provide the title compound as a white solid (1.9 g). 1H NMR δ 6.50 (m, 2H), 3.80 (s, 3H), 3.65 (s, 2H) | |
In water; N,N-dimethyl-formamide for 0.333333h; | 2.A A solution of KCN (0.88 g, 13 mmol) dissolved in water (2 mL) was added dropwise to a water-bath-cooled solution of 2,6-difluoro-4-methoxybenzyl bromide (2.50 g, 10.5 mmol) in N,N-dimethylformamide (10 mL). The reaction mixture was stirred for 20 min. Water was added (20 mL) and then the reaction mixture was poured into saturated aqueous NaHCC^ solution (20 mL) and extracted with ether (50 mL). The organic phase was washed with water (5 x 25 mL), dried over MgSC^, and concentrated to give an oil, which crystallized on standing to provide the title compound as a white solid (1.9 g)..H NMR δ 6.50 (m, 2H), 3.80 (s, 3H), 3.65 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: N,N-dimethyl-formamide; water / 0.33 h 2: sodium ethanolate / ethyl acetate; ethanol; xylene / 4 h / 50 °C 3: acetic acid / ethanol / 16 h / Reflux 4: copper(ll) bromide; tert.-butylnitrite / acetonitrile / 20 °C / Cooling with ice 5: potassium carbonate / palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 22 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; water / 0.33 h 2: sodium ethanolate / ethyl acetate; ethanol; xylene / 4 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide; water / 0.33 h 2: sodium ethanolate / ethyl acetate; ethanol; xylene / 4 h / 50 °C 3: acetic acid / ethanol / 16 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide; water / 0.33 h 2: sodium ethanolate / ethyl acetate; ethanol; xylene / 4 h / 50 °C 3: acetic acid / ethanol / 16 h / Reflux 4: copper(ll) bromide; tert.-butylnitrite / acetonitrile / 20 °C / Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58 mg | With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 5h; | 4-(2,6-Difluoro-4-methoxybenzyl)-2-(5,6-dimethylpyridin-3-yl)-2H-1 ,2,4- benzothiadiazin-3(4H)-one 1 ,1 -dioxide (178) 4-(2,6-Difluoro-4-methoxybenzyl)-2-(5,6-dimethylpyridin-3-yl)-2H-1 ,2,4- benzothiadiazin-3(4H)-one 1 ,1 -dioxide (178) The title compound (58 mg, 0.13 mmol) was prepared from 2-(5,6-dimethylpyridin-3- yl)-2/-/-1 ,2,4-benzothiadiazin-3(4/-/)-one 1 , 1-dioxide (lntA29) (150 mg, 0.49 mmol), 2,6-difluoro-4-methoxybenzyl bromide (129 mg, 0.54 mmol) and K2C03 (102 mg, 0.74 mmol) in DMF (3 mL) at 50°C using the methods of (115). LCMS (Method B): m/z 460.0 (M+H)+ (ES+), at 4.32 min, 95% 1H NMR: (400 MHz, CDCI3) δ: 2.38 (s, 3H), 2.60 (s, 3H), 3.77 (s, 3H), 5.45 (s, 2H), 6.43-6.51 (m, 2H), 7.35 (t, J=7.5, 1 H), 7.49-7.51 (m, 1 H), 7.62-7.73 (m, 2H), 7.93 (dd, J=7.8, 1.5, 1 H), 8.37 (d, J=2.3, 1 H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
301 mg | With potassium carbonate In N,N-dimethyl-formamide at 20 - 27℃; for 5h; | 1 Step 1 : Preparation of te/f-butyl {6-[4-(2,6-difluoro-4-methoxybenzyl)-1 , 1-dioxido-3- oxo-3,4-dihydro-2/-/-1 ,2,4-benzothiadiazin-2-yl]-3-methoxypyridin-2- yl}methyl carbamate Step 1 : Preparation of te/f-butyl {6-[4-(2,6-difluoro-4-methoxybenzyl)-1 , 1-dioxido-3- oxo-3,4-dihydro-2/-/-1 ,2,4-benzothiadiazin-2-yl]-3-methoxypyridin-2- yl}methyl carbamate The title compound (301 mg, 0.51 mmol) was prepared from te/f-butyl [6-(1 , 1- dioxido-3-oxo-3,4-dihydro-2H-1 ,2,4-benzothiadiazin-2-yl)-3-methoxypyridin-2- yl]methylcarbamate (lntA31) (343 mg, 0.79 mmol), 2,6-difluoro-4-methoxybenzyl bromide (225 mg, 0.95 mmol) and K2C03 (164 mg, 1.19 mmol) in DMF (4 ml_) at rt using the methods of (1 15). LCMS (Method B): m/z 591.2 (M+H)+ (ES+), at 5.04 min, 100% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38 mg | With potassium carbonate In N,N-dimethyl-formamide at 100℃; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92 mg | With potassium carbonate In N,N-dimethyl-formamide at 100℃; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38 mg | With potassium carbonate In N,N-dimethyl-formamide at 100℃; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59 mg | With potassium carbonate In N,N-dimethyl-formamide at 100℃; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: (S)-methyl-3,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinazoline-7-carboxylate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 5℃; for 0.25h; Inert atmosphere; Stage #2: 4-(bromomethyl)-3,5-difluorophenyl methyl ether In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h; | 149 Preiaration 51: (8)-Methyl 1-(2,6-difluoro-4-methoxybenzyfl-,4-dimethyl-2-oxo-1,2,,4-tetrahydro1uinazoline-7-carboxylate To a stirred solution of (S)-methyl 3,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinazoline-7- carboxylate (Preparation 14) (o.i g, 0.43 mmol) in DMF ( mL) was added NaH (0.014g, 60% suspension in mineral oil) at 0-5 oC under an inert atmosphere and the whole allowed to stir for 15 mm. Then, 2-(bromomethyl)-1,3-difluoro-5-methoxybenzene (0.119 g, 0.47 mmol) was added into the reaction mixture which was allowed to further stir at RT for 2 h. The progress of the reaction was monitored by TLC and LCMS and after completion the mixture was quenched with a saturated solution of NH4C1 andextracted with EtOAc. The organics were washed with cold water followed by brine, dried over anhydrous Na2SO4 and evaporated under reduced pressure to give titled compound (0.166 g, 100% yield and purity >95%) as a white solid. LCMS m/z: 391.14 [M+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 6.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / acetone / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 6.1: AD-mix-α / water; <i>tert</i>-butyl alcohol / 0 - 5 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 6.1: AD-mix-β / water; <i>tert</i>-butyl alcohol / 0 - 5 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C 3.2: 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C 3.2: 2 h / 20 °C 4.1: boron tribromide / dichloromethane / 0.5 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 - 5 °C 5.2: 0.67 h / 0 - 5 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: potassium carbonate / N,N-dimethyl-formamide / 0.25 h 5.2: 3 h / 60 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: 1H-tetrazole / acetonitrile / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: 1H-tetrazole / acetonitrile / 3 h / 20 °C 6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 - 5 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 - 5 °C 5.2: 0.67 h / 0 - 5 °C 6.1: sodium tetrahydroborate / ethanol / 3 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: potassium carbonate / N,N-dimethyl-formamide / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 - 5 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 20 °C 3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.25 h / 10 - 15 °C 3.2: 1 h / 20 °C 4.1: boron tribromide / dichloromethane / 2 h / 20 °C 5.1: potassium carbonate / N,N-dimethyl-formamide / 60 °C 6.1: trichlorophosphate / 1 h / 20 °C 6.2: 19 h / 0 - 5 °C |
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