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CAS No. : | 156642-03-4 | MDL No. : | MFCD04039030 |
Formula : | C13H13BO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VIHQQLWZRRVBNE-UHFFFAOYSA-N |
M.W : | 228.05 g/mol | Pubchem ID : | 4197354 |
Synonyms : |
|
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: |
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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 |
---|---|---|
85% | With palladium diacetate; potassium carbonate In acetone at 65℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | With palladium diacetate; potassium carbonate at 65℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In toluene at 110℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With n-butyllithium; Trimethyl borate; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 20℃; for 1h; | |
Stage #1: 4-bromo-4'-methoxylbiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78 - -65℃; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -65 - 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane at 20℃; Further stages.; | ||
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere 1.2: 17 h / -78 - 66 °C / Inert atmosphere 2.1: hydrogenchloride / water; tetrahydrofuran / 2 h / 23 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With sodium carbonate In ethanol; toluene for 2h; Heating / reflux; | 3-Methoxy-l-(4'-methoxy-4-biphenyl)naphthalene; A mixture of 3-methoxynaphthalen-l-yl trifluoromethanesulfonate (0.5 g, 1.7 mmol), (4'-methoxy-4-biphenyl)boronic acid (0.58 g, 2.5 mmol), Na2CO3 (0.27 g, 2.5 mmol) and Pd(PPh3 )4 (40 mg, 2 mol %) in PhMe (20 ml) and EtOH (20 ml) under N2 was heated at reflux. After 2 h the mixture was cooled, poured into water (100 ml), extracted with dichloromethane (3 x 50 ml), dried (MgSO4) and the solvent removed under reduced pressure. The residue was dissolved in dichloromethane, filtered through a short plug of silica and the solvent removed under reduced pressure to give the title compound (0.44 g, 76 %) as a colourless powder. |
76% | With sodium carbonate In ethanol; toluene for 2h; Heating / reflux; | 3-Methoxy-l-(4'-methoxy-4-biphenyl)naphthalene; A mixture of 3-methoxynaphthalen-l-yl trifluoromethanesulfonate (0.5 g, 1.7 mmol), (4'-methoxy-4-biphenyl)boronic acid (0.58 g, 2.5 mmol), Na2CO3 (0.27 g, 2.5 mmol) and Pd(PPh3)4 (40 mg, 2 mol %) in PhMe (20 ml) and EtOH (20 ml) under N2 was heated at reflux. After 2 h the mixture was cooled, poured into water (100 ml), extracted with dichloromethane (3 x 50 ml), dried (MgSO4) and the solvent removed under reduced pressure. The residue was dissolved in dichloromethane, filtered through a short plug of silica and the solvent removed under reduced pressure to give the title compound (0.44 g, 76 %) as a colourless powder. |
76% | With sodium carbonate In ethanol; toluene for 2h; Heating / reflux; | 3-Methoxy-l-(4'-methoxy-4-biphenyl)naphthalene; A mixture of 3-methoxynaphthalen-l-yl trifluoromethanesulfonate (0.5 g, 1.7 mmol), (4'-methoxy-4-biphenyl)boronic acid (0.58 g, 2.5 mmol), Na2CO3 (0.27 g, 2.5 mmol) and Pd(PPh3)4 (40 mg, 2 mol %) in PhMe (20 ml) and EtOH (20 ml) under N2 was heated at reflux. After 2 h the mixture was cooled, poured into water (100 ml), extracted with dichloromethane (3 x 50 ml), dried (MgSO4) and the solvent removed under reduced pressure. The residue was dissolved in dichloromethane, filtered through a short plug of silica and the solvent removed under reduced pressure to give the title compound (0.44 g, 76 %) as a colourless powder. |
76% | With sodium carbonate In ethanol; dichloromethane; toluene | 3-Methoxy-1-(4'-methoxy-4-biphenyl)naphthalene 3-Methoxy-1-(4'-methoxy-4-biphenyl)naphthalene A mixture of 3-methoxynaphthalen-1-yl trifluoromethanesulfonate (0.5 g, 1.7 mmol), (4'-methoxy-4-biphenyl)boronic acid (0.58 g, 2.5 mmol), Na2CO3 (0.27 g, 2.5 mmol) and Pd(PPh3)4 (40 mg, 2 mol %) in PhMe (20 ml) and EtOH (20 ml) under N2 was heated at reflux. After 2 h the mixture was cooled, poured into water (100 ml), extracted with dichloromethane (3*50 ml), dried (MgSO4) and the solvent removed under reduced pressure. The residue was dissolved in dichloromethane, filtered through a short plug of silica and the solvent removed under reduced pressure to give the title compound (0.44 g, 76%) as a colourless powder. |
76% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene for 2h; Inert atmosphere; Reflux; | 3-Methoxy-1-(4'-methoxy-4-biphenyl)naphthalene 3-Methoxy-1-(4'-methoxy-4-biphenyl)naphthalene A mixture of 3-methoxynaphthalen-1-yl trifluoromethanesulfonate (0.5 g, 1.7 mmol), (4'-methoxy-4-biphenyl)boronic acid (0.58 g, 2.5 mmol), Na2CO3 (0.27 g, 2.5 mmol) and Pd(PPh3)4 (40 mg, 2 mol %) in PhMe (20 ml) and EtOH (20 ml) under N2 was heated at reflux. After 2 h the mixture was cooled, poured into water (100 ml), extracted with dichloromethane (3*50 ml), dried (MgSO4) and the solvent removed under reduced pressure. The residue was dissolved in dichloromethane, filtered through a short plug of silica and the solvent removed under reduced pressure to give the title compound (0.44 g, 76%) as a colourless powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With sodium carbonate In tetrahydrofuran; water for 48h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With silver hexafluoroantimonate; tetrafluoroboric acid In water; isopropyl alcohol at 10℃; for 21h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In various solvent(s) at 85℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 51 percent / Na2CO3 / tetrakis(triphenylphosphine) palladium(0) / H2O; tetrahydrofuran / 48 h / Heating 2: 68.2 percent / ICl / CH2Cl2 / 0.5 h / -78 °C 3: 89.7 percent / BBr3 / CH2Cl2 / 6 h / 20 °C 4: 53 percent / K2CO3 / acetone; ethanol / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 51 percent / Na2CO3 / tetrakis(triphenylphosphine) palladium(0) / H2O; tetrahydrofuran / 48 h / Heating 2: 68.2 percent / ICl / CH2Cl2 / 0.5 h / -78 °C 3: 89.7 percent / BBr3 / CH2Cl2 / 6 h / 20 °C 4: 53 percent / K2CO3 / acetone; ethanol / 2 h / Heating 5: 73 percent / K2CO3 / acetonitrile / 12 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 51 percent / Na2CO3 / tetrakis(triphenylphosphine) palladium(0) / H2O; tetrahydrofuran / 48 h / Heating 2: 68.2 percent / ICl / CH2Cl2 / 0.5 h / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 51 percent / Na2CO3 / tetrakis(triphenylphosphine) palladium(0) / H2O; tetrahydrofuran / 48 h / Heating 2: 68.2 percent / ICl / CH2Cl2 / 0.5 h / -78 °C 3: 89.7 percent / BBr3 / CH2Cl2 / 6 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 51 percent / Na2CO3 / tetrakis(triphenylphosphine) palladium(0) / H2O; tetrahydrofuran / 48 h / Heating 2: 68.2 percent / ICl / CH2Cl2 / 0.5 h / -78 °C 3: 89.7 percent / BBr3 / CH2Cl2 / 6 h / 20 °C 4: 56 percent / K2CO3 / acetonitrile / 12 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2: BBr3 / CH2Cl2 / 10 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: NaBH4 / trifluoroacetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: Br2; KOAc / acetic acid / 0.17 h / 5 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: Br2; KOAc / acetic acid / 0.17 h / 5 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: Br2; KOAc / acetic acid / 0.17 h / 5 °C 6.1: (dppf)PdCl2; K2CO3 / 1,2-dimethoxy-ethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: Br2; KOAc / acetic acid / 0.17 h / 5 °C 6.1: K2CO3 / dimethylformamide / 2 h / 75 °C 7.1: NaOH / methanol; tetrahydrofuran / 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: Br2; KOAc / acetic acid / 0.17 h / 5 °C 6.1: K2CO3 / dimethylformamide / 2 h / 75 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: Br2; KOAc / acetic acid / 0.17 h / 5 °C 6.1: (dppf)PdCl2; K2CO3 / 1,2-dimethoxy-ethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: Br2; KOAc / acetic acid / 0.17 h / 5 °C 6.1: (dppf)PdCl2; K2CO3 / 1,2-dimethoxy-ethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: NaBH4 / trifluoroacetic acid 5.1: diethylazodicarboxylate; PPh3 / benzene / 0.5 h / 20 °C 6.1: NaOH / methanol; tetrahydrofuran / 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: NaBH4 / trifluoroacetic acid 5.1: diethylazodicarboxylate; PPh3 / benzene / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: Br2; KOAc / acetic acid / 0.17 h / 5 °C 6.1: K2CO3 / dimethylformamide / 2 h / 75 °C 7.1: NaOH / methanol; tetrahydrofuran / 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: Br2; KOAc / acetic acid / 0.17 h / 5 °C 6.1: (dppf)PdCl2; K2CO3 / 1,2-dimethoxy-ethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: NaBH4 / trifluoroacetic acid 5.1: diethylazodicarboxylate; PPh3 / benzene / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: NaBH4 / trifluoroacetic acid 5.1: diethylazodicarboxylate; PPh3 / benzene / 0.5 h / 20 °C 6.1: NaOH / methanol; tetrahydrofuran / 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: Br2; KOAc / acetic acid / 0.17 h / 5 °C 6.1: K2CO3 / dimethylformamide / 2 h / 75 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: Br2; KOAc / acetic acid / 0.17 h / 5 °C 6.1: (dppf)PdCl2; K2CO3 / 1,2-dimethoxy-ethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: diethylazodicarboxylate; PPh3 / benzene / 0.5 h / 20 °C 6.1: NaOH / methanol; tetrahydrofuran / 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: Br2; KOAc / acetic acid / 0.17 h / 5 °C 6.1: (dppf)PdCl2; K2CO3 / 1,2-dimethoxy-ethane 7.1: K2CO3 / dimethylformamide / 2 h / 75 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: diethylazodicarboxylate; PPh3 / benzene / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: diethylazodicarboxylate; PPh3 / benzene / 0.5 h / 20 °C 6.1: NaOH / methanol; tetrahydrofuran / 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: diethylazodicarboxylate; PPh3 / benzene / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 85 percent / Pd(OAc)2; aq. K2CO3 / acetone / 2 h / 65 °C 2.1: BBr3 / CH2Cl2 / 10 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 3 h / -40 °C 3.2: tetrahydrofuran / 0.5 h / 0 °C 4.1: hydrazine monohydrate; diethylene glycol / 1 h / 180 °C 4.2: KOH / 10 h / 130 °C 5.1: diethylazodicarboxylate; PPh3 / benzene / 0.5 h / 20 °C |
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