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Basic Information
| CAS No.: | 944129-07-1 |
|---|---|
| Name: | 4-Chloro-2-fluoro-3-methoxyphenylboronic acid |
| Article Data: | 6 |
| Molecular Structure: | |
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|
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| Formula: | C7H7BClFO3 |
| Molecular Weight: | 204.393 |
| Synonyms: | (4-chloro-2-fluoro-3-methoxyphenyl)-boronic acid; |
| Density: | 1.40±0.1 g/cm3(Predicted) |
| Boiling Point: | 342.7±52.0 °C(Predicted) |
| PSA: | 49.69000 |
| LogP: | 0.16750 |
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Synthetic route
- 53145-38-3
1-chloro-3-fluoro-2-methoxybenzene
- 944129-07-1
(4-chloro-2-fluoro-3-methoxy-phenyl)boronic acid
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: 1-chloro-3-fluoro-2-methoxybenzene With n-butyllithium In 1,2-dimethoxyethane at -78 - -70.1℃; for 1.75h; Stage #2: With Trimethyl borate In 1,2-dimethoxyethane at -67 - 20℃; Time; Temperature; Further stages; | 93% |
| Multi-step reaction with 2 steps 1.1: n-butyllithium / 1,2-dimethoxyethane; hexane / 1.75 h / -77 - -70.1 °C / Inert atmosphere 1.2: 1.37 h / -74.1 - 23.1 °C 2.1: potassium hydroxide; water / 1,2-dimethoxyethane / 2 h / 30 °C / Cooling View Scheme |
- 121-43-7
Trimethyl borate
- 53145-38-3
1-chloro-3-fluoro-2-methoxybenzene
- 944129-07-1
(4-chloro-2-fluoro-3-methoxy-phenyl)boronic acid
Conditions
| Conditions | Yield |
|---|---|
| With n-butyllithium In tetrahydrofuran; hexane; cyclohexane at -50℃; Flow reactor; | 92% |
| Stage #1: 1-chloro-3-fluoro-2-methoxybenzene With n-butyllithium In 1,2-dimethoxyethane at -65℃; Inert atmosphere; Stage #2: Trimethyl borate In 1,2-dimethoxyethane at -65 - 30℃; Time; Inert atmosphere; |
- 121-43-7
Trimethyl borate
- 944129-07-1
(4-chloro-2-fluoro-3-methoxy-phenyl)boronic acid
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: Trimethyl borate; 6-chloro-2-fluoro-3-lithioanisole In 1,2-dimethoxyethane; hexane at -70 - -45℃; for 0.25h; Cooling with dry ice bath; Stage #2: With hydrogenchloride; water In 1,2-dimethoxyethane; hexane Product distribution / selectivity; | |
| Stage #1: Trimethyl borate; 6-chloro-2-fluoro-3-lithioanisole In hexanes; 1,2-dimethoxyethane at -65 - 20℃; Stage #2: With potassium hydroxide; water In hexanes; 1,2-dimethoxyethane at 23.1℃; for 1.11667h; Stage #3: With hydrogenchloride In water; acetonitrile Product distribution / selectivity; | |
| Stage #1: Trimethyl borate; 6-chloro-2-fluoro-3-lithioanisole In hexanes; 1,2-dimethoxyethane at -65 - 20℃; Stage #2: With potassium hydroxide; water In hexanes; 1,2-dimethoxyethane at 23.3℃; for 1.43333h; Stage #3: With hydrogenchloride In water Product distribution / selectivity; |
- 1426539-30-1
4-chloro-2-fluoro-3-methoxyphenyl dimethylboronate
- 944129-07-1
(4-chloro-2-fluoro-3-methoxy-phenyl)boronic acid
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: 4-chloro-2-fluoro-3-methoxyphenyl dimethylboronate With water; potassium hydroxide at 16 - 20℃; for 0.25h; Stage #2: With hydrogenchloride In water for 0.25h; | |
| With water; potassium hydroxide In 1,2-dimethoxyethane at 30℃; for 2h; Cooling; |
- 76-09-5
2,3-dimethyl-2,3-butane diol
- 944129-07-1
(4-chloro-2-fluoro-3-methoxy-phenyl)boronic acid
- 1126321-06-9
2-(4-chloro-2-fluoro-3-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions
| Conditions | Yield |
|---|---|
| In ethyl acetate at 23.1℃; for 2h; Inert atmosphere; | 99% |
- 496850-09-0
methyl 4-amino-3,6-dichloro-5-fluoropicolinate
- 944129-07-1
(4-chloro-2-fluoro-3-methoxy-phenyl)boronic acid
Conditions
| Conditions | Yield |
|---|---|
| With palladium diacetate; potassium carbonate; triphenylphosphine In methanol; water; acetonitrile at 60℃; for 7h; Suzuki Coupling; | 88.1% |
Conditions
| Conditions | Yield |
|---|---|
| With dichloro[9,9-dimethyl-4,5- bis(diphenylphosphino)xanthene]palladium (II); triethylamine In water; toluene at 55℃; for 24h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Suzuki-Miyaura Coupling; Inert atmosphere; | 85% |
- 350601-39-7
methyl 4-amino-3,6-dichloropyridine-2-carboxylate
- 944129-07-1
(4-chloro-2-fluoro-3-methoxy-phenyl)boronic acid
Conditions
| Conditions | Yield |
|---|---|
| With palladium diacetate; potassium carbonate; triphenylphosphine In water; acetonitrile at 50℃; for 22h; Concentration; Reagent/catalyst; Suzuki Coupling; Inert atmosphere; | 81.4% |
| With bis-triphenylphosphine-palladium(II) chloride; potassium fluoride In water; acetonitrile for 4h; Reflux; |
- 944129-07-1
(4-chloro-2-fluoro-3-methoxy-phenyl)boronic acid
- 1390662-56-2
benzyl 4,5,6-trichloropicolinate
- 1390662-58-4
benzyl 4,5-dichloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)picolinate
Conditions
| Conditions | Yield |
|---|---|
| With dichloro[9,9-dimethyl-4,5- bis(diphenylphosphino)xanthene]palladium (II); triethylamine In water; toluene at 35℃; for 18h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Suzuki-Miyaura Coupling; Inert atmosphere; | 79% |
- 944129-07-1
(4-chloro-2-fluoro-3-methoxy-phenyl)boronic acid
- 1126320-49-7
methyl 6-amino-2-chloro-5-methoxy-pyrimidine-4-carboxylate
- 1126318-85-1
methyl 6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-methoxypyrimidine-4-carboxylate
Conditions
| Conditions | Yield |
|---|---|
| With palladium diacetate; potassium hydrogencarbonate; triphenylphosphine In methanol; water; acetonitrile at 50℃; for 22h; Suzuki Coupling; Inert atmosphere; | 75.6% |
| With cesium fluoride; bis-triphenylphosphine-palladium(II) chloride In 1,2-dimethoxyethane; water at 100℃; for 0.25h; Microwave irradiation; | 51.1% |
