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With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In water; N,N-dimethyl-formamide; at 80.0℃; for 0.666667h;Inert atmosphere;
Reference Example 311-(Biphenyl-2-yl)cyclopropane-carboxylic acid (Step 1)<strong>[124276-87-5]1-(2-Bromophenyl)cyclopropane-carboxylic acid</strong> (2.00 g) and phenylboronic acid (1.52 g) was dissolved in N,N-dimethylformamide (48 ml), and to the reaction was added [1,1'-bis(diphenylphosphino)ferrocene]palladium (II) dichloride.dichloromethane complex (0.34 g) and 2 N sodium carbonate aqueous solution (12 ml). After substituting with nitrogen, the mixture was stirred for 40 hours with heating at 80 C. The solvent was evaporated under reduced pressure, 2 N sodium hydroxide aqueous solution was added to the residue, and the insoluble precipitate was removed by Celite filtration. The filtrate was washed with ethyl acetate, and treated with concentrated hydrochloric acid to adjust to pH 1. The mixture was extracted with ethyl acetate, washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified on silica gel column chromatography to give 1-(biphenyl-2-yl)cyclopropane-carboxylic acid as a white crystal (1.58 g).1H-NMR (DMSO-d6) delta: 0.77 (br, 2H), 1.20 (br, 2H), 7.19-7.21 (m, 1H), 7.30-7.44 (m, 8H).
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).
1-bromo-2-(1-(trifluoromethyl)cyclopropyl)benzene[ No CAS ]
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.
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