4-Bromo-2,6-difluorobenzoic acid
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4-Bromo-2,6-difluorobenzoic acid
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CAS No:
183065-68-1
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Formula:
C7H3BrF2O2
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Chemical Name:
4-Bromo-2,6-difluorobenzoic acid
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Synonyms:
Benzoic acid,4-bromo-2,6-difluoro-;4-Bromo-2,6-difluorobenzoic acid;2,6-Difluoro-4-bromobenzoic acid
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CAS No:
Characteristics
37.3
2.3
Off-white Cryst
1.9±0.1 g/cm3
196-198 °C @ Solvent: Hexane
271.7°C at 760 mmHg
118.1±27.3 °C
1.559
Room temperature.
Safety Information
IRRITANT
NONH for all modes of transport
22-36/37/38
26-37
Xi,Xn
Irritant
P305 + P351 + P338
H302-H319
|Warning|H302 (81.25%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 48 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, and P362|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
4-Bromo-2,6-difluorobenzoic acid Use and Manufacturing
70 mL of THF was cooled to -78°C, and diisopropylamine (4 mL, 28.5 mmol) and butyllithium (13 mL, 27.2mmol, 2.1 M hexane solution) were sequentially added thereto. The mixture was stirred at -78°C for 1 hour, and 1-bromo-3, 5-difluorobenzene (5.0 g, 25.9 mmol) dissolved in 15 mL was slowly added thereto. The mixture was stirred at -78°Cfor 45 minutes, and the reaction solution was transferred to a beaker containing solid carbon dioxide and stirred at roomtemperature for 16 hours. The reaction solution was adjusted to pH 3 by the addition of 1N HCl aqueous solution andextracted with EtOAc. The organic layer was collected and dried with MgSO4 to obtain the title compound (5.15 g, 84 percent).1H-NMR (CDCl3) δ 7.20 (2H, m)(1) in the reaction bottle, by adding 0.65mol (1.3eq) diisopropylamine, 365 ml THF, stirring, lower the temperature to -30 °C, efficient adds by drops positively 0.5mol (1.0eq), thermal insulation reaction completion of the dropping, the reaction time, to continue to lower the temperature to -70.0°C, start dropping raw material 3, 5-difluoro-bromobenzene 0.5mol, completion of the dropping, thermal reaction, to the reaction time, to continue to pass carbon dioxide 1.5mol (3.0eq), after the carbon dioxide passes, to continue to heat insulation reaction, until the raw material the reaction end, concentrated heating, water, acid hydrolysis instillment salt, adjusting PH to 1-2, thermal reaction, to the reaction time, drained, beating purification, the white solid obtained after drying 4-bromo -2, 6-difluoro-benzoic acid 0.37mol, moisture 0.48percent, purity 98.9percent, yield of 74.0percent.Synthesis of 3-AMINO-6-BROMO-4-CYCLOPENTYLMETHOXY- BENZO [B] THIOPHENE-2, 7-dicarboxylic acid diamide To a stirred solution of 3, 5-difluorobromobenzene (20 g, 103.6 mmol) in THF (200 mL) AT-78 °C was added lithium diisopropylamide (2.0 M, 51 mL, 103 mmol). The reaction was stirred for 1.5 h. Then it was poured slowly onto dry ice and stirred until it reached room temperature. The mixture was concentrated to about 10 mL and then diluted with 6 N HC1 (200 mL), extracted with dichloromethane (200 mL). The solution was dried over NA2S04 and the solvent was removed in vacuo to give 4-bromo-2, 6-difluorobenzoic acid (18 g, 73. 3percent).H2) 4-Bromo-2, 6-difluorobenzoic acid A solution of diisoporpylamine (32 g, 0.31 mol) in THF (170 ml) is added n-BuLi (116 ml, 0.30 mol) drop wise, while keeping inner temperature below -65° C. The mixture is stirred at -50° C. for 1 h to get LDA solution. To a solution of compound H1 (50 g, 0.26 mol) in THF (170 mL) is added LDA, while keeping inner temperature below -65° C., then stirred for 1.5 h and COTo a solution of 1-bromo-3, 5-difluorobenzene (1 g, 5.2 mmol) in dry tetrahydrofuran (50 mL), was added lithium diisopropylamide (0.557 g, 5.2 mmol) at -78° C. The resulting reaction mixture was stirred at an ambient temperature for about 1.5 hours. A cooled reaction mixture was poured onto dry ice and left for about 20 minutes, followed by mixing with aqueous hydrochloric acid (6N, 10 mL). The acidic aqueous phase was extracted with ethyl acetate (3*100 mL). The combined organic layer dried over anhydrous sodium sulfate, filtered and concentrated to afford 4-bromo-2, 6-difluorobenzoic acid (800 mg, 66.66percent). Step: 2 4-bromo-2, 6-difluorobenzoic acid
Computed Properties
Molecular Weight:237.00
XLogP3:2.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:235.92845
Monoisotopic Mass:235.92845
Topological Polar Surface Area:37.3
Heavy Atom Count:12
Complexity:176
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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