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CAS No. : | 124276-87-5 | MDL No. : | MFCD07374434 |
Formula : | C10H9BrO2 | Boiling Point : | 366.4°C at 760 mmHg |
Linear Structure Formula : | - | InChI Key : | N/A |
M.W : | 241.08 | Pubchem ID : | 20026176 |
Synonyms : |
|
TPSA :Topological Polar Surface Area | 37.3 | H-Bond Acceptor Count : | 2 |
XLogP3 : | 2.4 | H-Bond Donor Count : | 1 |
SP3 : | 0.30 | Rotatable Bond Count : | 2 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfur tetrafluoride; hydrogen fluoride; In dichloromethane; at 100.0℃; for 36.0h;Autoclave; | 1-(2-Bromo-phenyl)cyclopropane carboxylic acid acid (1 eq.) (commercially available, Combi-Blocks) was placed in an autoclave and to this was added dichloromethane (2 vol), anhydrous HF (2 eq.), followed by SF4 (3 eq.). The vessel was then heated to 100C for 36 h. The reaction was cooled to rt, transferred to a 5 L vessel of ice (1 vol) and washed with dichloromethane (0.5 vol). The solution was carefully basified with a solution of potassium hydrogen carbonate. Once the solution reached pH 8 the mixture was separated and the aqueous layer extracted with dichloromethane (2 x 1 vol). The combined organic layers were dried (MgS04), filtered and concentrated at atmospheric pressure to yield the acid fluoride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With hydrogenchloride; In water; at 20.0℃; for 40.0h;Reflux; | (a) Methyl 1-(2-bromophenyl)cyclopropanecarboxylate (14)A solution of <strong>[124276-87-5]1-(2-bromophenyl)cyclopropanecarboxylic acid</strong> (500 mg, 2.07 mmol) inMeOH (10 mL) was treated with a solution of concentrated aqueous HCI (0.5 mL).The resulting mixture was stirred for 16 hours at room temperature and then heated to reflux and stirred for a further 24 hours. The volatiles were evaporated and the residue was dissolved in EtOAc. The organic layer was washed with saturated solution of NaHCO3, brine and then dried over MgSO4. The solvent was removed invacuo to give the title compound 14 (400 mg, 76%) as an orange oil; 1H NMR (400 MHz, ODd3) O 7.60-7.54 (m, 1H), 7.32-7.24 (m, 2H), 7.15 (m, 1H), 3.63 (5, 3H), 1.75 (d, J= 3.1 Hz, 2H), 1.21 (q, J= 4.0 Hz, 2H). |
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