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[ CAS No. 6142-65-0 ] {[proInfo.proName]}

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Chemical Structure| 6142-65-0
Chemical Structure| 6142-65-0
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Product Details of [ 6142-65-0 ]

CAS No. :6142-65-0 MDL No. :MFCD29055398
Formula : C10H9BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :DPBUJVBXRABXRH-DTWKUNHWSA-N
M.W : 241.08 Pubchem ID :12586658
Synonyms :

Safety of [ 6142-65-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6142-65-0 ]

* 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.

  • Downstream synthetic route of [ 6142-65-0 ]

[ 6142-65-0 ] Synthesis Path-Downstream   1~56

  • 1
  • [ 53582-00-6 ]
  • [ 6142-65-0 ]
YieldReaction ConditionsOperation in experiment
99% With sodium hydroxide; In ethanol; water; at 20℃; for 5h; General procedure: To the cooled solution of 1 g NaOH (25 mmol) in 4 cm3 EtOH/H2O (85/15; v/v) was added the solution of esters 18-20 (2.21 mmol) in 9 cm3 EtOH. The reaction mixture was stirred at room temperature for 5 h and then the solvents were removed under reduced pressure. The residue was dissolved in 30 cm3 water and washed with 2*15 cm3 CH2Cl2. An aqueous layer was acidified with concentrated HCl and extracted with 3*15 cm3 CH2Cl2. The organic layers were combined and dried over Na2SO4 and evaporated to dryness.
72% NaOH 4N (20 mL) was added to a solution of (trans)-et yl 2-(4- bromophenyl)cyclopropanecarboxylate (Intermediate I, 4 g, 0.0149 mol), in Methanol (40 mL) and stirred at rt for 2 h. After completion of reaction, checked by TLC, the solvent was evaporated and the residue was diluted with water (50 mL), acidified with HCl 4 N solution, the solid formed was filtered and dried to get (trans)-2-(4- bromophenyl)cyclopropanecarboxylic acid (2.59 g, 72 %), as a white solid.
Intermediate 3: 7rans-2-(4~bromophenyl)cyclopropanecarboxylic acid racemic; To a solution of racemic frans-ethyl 2-(4-bromophenyl)cyclopropanecarboxylate (Intermediate 2) (4.97g, 18.47mmol) in 76.72 mL of EtOH was added dropwise 49.08mL of 2N NaOH and the mixture was stirred at room temperature for 1h. The solution was then concentrated in vacuo, 2OmL of water were added and the aqueous phase washed with 2x20mL Et2O. The aqueous phase was then acidified with 2M HCI to pH 3 (approx.) and extracted with 3x10OmL Et2O. The collected organic phases were dried over Na2SO4, filtered and concentrated in vacuo to get EPO <DP n="39"/>4.43g of the title compound as a white solid, which was used in the next step without further purification.NMR (de-DMSO): 12.36 (bs, 1 H), 7.44 (d, 2H), 7.13 (d, 2H), 2.38 (m, 1 H), 1.80 (m,1 H), 1.42 (m, 1 H), 1.32 (m, 1 H).
ii) trans-(+/-)-2-(4-Bromo-phenyl)-cyclopropanecarboxylic acid; A solution of .ra/7S-(+/-)-ethyl 2-(4-Bromo-phenyl)cyclopropanecarboxylate (950 mg, 3.53 mmol) in MeOH (7.5 mL) was added to KOH (1.98 g, 35.3 mmol) in MeOH (10 ml_) at 0 C. The mixture was stirred at room temperature overnight and then poured into water and extracted with CH2CI2. The organic layer was discarded and the aqueous phase was acidified with 10% HCI and extracted with CH2CI2 (x2). The combined organic phases were dried over Na2SO4 and all volatiles were removed under vacuum. The acid was isolated as white powders and further purified by recrystallization from hexane (847 mg).
With lithium hydroxide; In tetrahydrofuran; methanol; at 50℃; for 1h;Alkaline conditions; To a solution of ester from step 1 in THF-MEOH (4: 1,0. 5M) was added LIOH (3 eq, 2M) and the mixture was stirred at 50C for LH. The organic solvent evaporated, aqueous was acidified with HCl 1N and the acid extracted with EtOAc (3X). The organic was washed with brine, dried and solvent evaporated to afford 2- (4-bromophenyl) cyclopropanecarboxylic acid. Optically active precursors are obtained by separation on chiral column (Chiral Pak AD) eluting with hexane: EtOH or hexane: iPrOH containing 0. 2% TFA.
2.59 g With water; sodium hydroxide; In methanol; at 20℃; for 2h; Intermediate P: (Trans)-2-(4-bromophenNaOH 4N (20 mL) was added to a solution of (frans)-ethyl 2-(4-bromophenyl)cyclopropanecarboxylate (Intermediate O, 4 g, 0.0149 mol), in Methanol (40 mL) and stirred at rt for 2 h. After completion of reaction, checked by TLC, the solvent was evaporated and the residue was diluted with water (50 mL), acidified with HCI 4 N solution, the solid formed was filtered and dried to get (frans)-2-(4-bromophenyl)cyclopropanecarboxylic acid (2.59 g, 72 %), as a white solid
2.59 g With water; sodium hydroxide; In methanol; at 20℃; for 2h; Intermediate P: (Trans)-2-(4-bromophenNaOH 4N (20 mL) was added to a solution of (frans)-ethyl 2-(4-bromophenyl)cyclopropanecarboxylate (Intermediate O, 4 g, 0.0149 mol), in Methanol (40 mL) and stirred at rt for 2 h. After completion of reaction, checked by TLC, the solvent was evaporated and the residue was diluted with water (50 mL), acidified with HCI 4 N solution, the solid formed was filtered and dried to get (frans)-2-(4-bromophenyl)cyclopropanecarboxylic acid (2.59 g, 72 %), as a white solid

  • 2
  • [ 134198-10-0 ]
  • [ 6142-65-0 ]
YieldReaction ConditionsOperation in experiment
Example 29C; 2-(4-Brorno-phenv?-trans-cvclopropanecarboxylic acid (racemic); A solution of the product from Example 29B (24.3 g, 86 mmol) and potassium t-butoxide (80.8 g, 684 mmol) in diethyl ether (900 mL) and water (10 mL) was stirred at room temperature for three days. The mixture was then slowly <n="86"/>acidified by the addition of concentrated hydrochloric acid. The ether layer was washed with brine and the acidic aqueous layer was extracted with ethyl acetate (2 X 100 mL). The ether layer and the ethyl acetate extracts were combined, dried (MgStheta4), and filtered. The filtrate was concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz1 CDCI3): delta 1.33-1.42 (m, 1H), 1.63-1.71 (m, 1H), 1.84-1.91 (m, 1H), 2.51-2.60 (m, 1H), 6.98 (d, J = 9 Hz, 2H), 7.41 (d, J = 9 Hz, 2H)1 11.08 (br s, 1 H). MS (DCI-NH3) m/z 258 (M+NH4)+.
  • 3
  • (+-)-<i>trans</i>-2-<4-bromo-phenyl>-cyclopropanecarboxylic acid ethyl ester [ No CAS ]
  • [ 6142-65-0 ]
  • 4
  • [ 1885-28-5 ]
  • [ 6142-65-0 ]
  • 5
  • [ 100115-96-6 ]
  • [ 6142-65-0 ]
  • 6
  • [ 6142-65-0 ]
  • [ 1123620-89-2 ]
  • [ 31501-85-6 ]
YieldReaction ConditionsOperation in experiment
Resolution of racemate; To a solution of ester from step 1 in THF-MEOH (4: 1,0. 5M) was added LIOH (3 eq, 2M) and the mixture was stirred at 50C for LH. The organic solvent evaporated, aqueous was acidified with HCl 1N and the acid extracted with EtOAc (3X). The organic was washed with brine, dried and solvent evaporated to afford 2- (4-bromophenyl) cyclopropanecarboxylic acid. Optically active precursors are obtained by separation on chiral column (Chiral Pak AD) eluting with hexane: EtOH or hexane: iPrOH containing 0. 2% TFA.
  • 7
  • [ 6142-65-0 ]
  • [ 75-65-0 ]
  • (±)-trans-O-tert-butyl-N-(2-(4-bromophenyl)cyclopropyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With diphenylphosphoranyl azide; triethylamine; for 24h;Reflux; General procedure: To a solution of the corresponding (±)-trans-2-phenylcyclopropane-1-carboxylic acid, 21-25 (2.0 mmol) in 5 cm3 dry tert-butyl alcohol (for 1-4) or 5 cm3 dry toluene (for 5-7) or 5 cm3 dry 1,4-dioxane (for 8) corresponding alcohol (2.4 mmol) (except for 1-4), 0.43 cm3 diphenylphosphoryl azide (2.0 mmol) and 0.33 cm3 TEA (2.4 mmol) were added. The mixture was heated to reflux for 24 h, and then the solvent was removed under reduced pressure. The residue was dissolved in 20 cm3 CH2Cl2 and the solution was washed with 2*25 cm3 saturated sodium bicarbonate and 2*25 cm3 brine. The organic layer was dried over Na2SO4, concentrated under reduced pressure and purified by column chromatography on silica gel [EtOAc/n-hexane (1/1)].
With diphenylphosphoranyl azide; triethylamine; at 90℃; Intermediate 4: Trans-1, 1-dimethylethyl [2-(4-bromophenyl)cyclopropyl] carbamate racemic; To a solution of of racemic frans-1 ,1-dimethylethyl [2-(4- bromophenyl)cyclopropyl]carbamate (Intermediate 3) (4.32g, 17.92mmol) in 55.4ml_ of dry 4BuOH was added TEA (3.5ml_, 24.73mmol) and diphenylphosphoryl azide(4.24mL, 19.71 mmol). The mixture was stirred at 900C under nitrogen overnight then concentrated in vacuo and poured into 10% aqueous Na2CO3 The aqueous phase was extracted with 3 x 30OmL Et2O and the collected organics dried over Na2SO4 and concentrated in vacuo to get crude material (8.65g) that was purified by SiO2 flash chromatography (Horizon 65M) eluting with cyclohexane/ethyl acetate from90/10 to 80/20. Evaporation of the solvent in vacuo afforded 2.1g of pure title material as an off white solid.NMR (CDCI3): 7.38 (d, 2H), 7.03 (d, 2H), 4.82 (bs, 1 H), 2.68 (m, 1 H), 2.02 (m, 1 H),1.46 (s, 9H), 1.14 (m, 2H).
  • 8
  • [ 6142-65-0 ]
  • trans-(+/-)-2-(4-bromo-phenyl)-cyclopropanecarboxylic acid chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride;N,N-dimethyl-formamide; In toluene; at 80℃; for 3h; iii) frans-(+/-)-2-(4-Bromo-phenyl)-cyclopropanecarboxylic acid amide; To a solution of trans-(+/-)-2-(4-Bromo-phenyl)cyclopropanecarboxylic acid (400 mg, 1.66 mmol) in toluene (6 mL) were added dropwise a few drops of dimethylformamide and thionyl chloride (1.82 mL, 24.9 mmol). After stirring at 80 C for 3 h, the reaction mixture was concentrated under vacuum. The resulting residue was dissolved in toluene (2 mL) again, and the solution was added to liquid ammonia (ca. 20 mL) at -78 C. After stirring at -78 C for 30 min and then at room temperature for 30 min, CH2CI2 (25 ml) was added to the mixture at -78 C and the resulting mixture was stirred at room temperature overnight. After addition of EtOAc, the mixture was washed with satd. aqueous NH4CI (x2), dried over Na2SO4 and all volatiles were removed under vacuum. The title compound was isolated as pearl yellow powders and further purified by recrystallization from hexane/EtOAc (282 mg).
  • 10
  • [ 3886-70-2 ]
  • [ 6142-65-0 ]
  • [ 1332345-01-3 ]
YieldReaction ConditionsOperation in experiment
In ethanol; water; at 20℃; for 4h; To a stirred solution of <strong>[6142-65-0](trans)-2-(4-bromophenyl)cyclopropanecarboxylic acid</strong> (6.52 g, 27.04 mmol), which can be prepared in accordance with the process set forth on page 82 of WO 2009/024823, in 400 ml of EtOH was added a solution of (R)-(+)-1-(1-Naphthyl)ethylamine (4.63g, 4.37 mL, 27.04 mmol), in 100 ml of EtOH followed by 25 ml of H2O. This was stirred at rt for about 4 h. The solid was collected by filtration and washed with 40 ml of cold EtOH/H2O (20/1) providing 3.18 grams of salt as a white solid (58% recovery) equivalent to 1.86 g of free acid. This was taken up in 2 N NaOH and extracted 5×s with EtOAc. The aq. phase was placed on a rotary evaporator to remove the remaining EtOAc. The resulting clear solution was transferred to an erlenmeyer flask, cooled in an ice bath, and conc. HCl was added dropwise while stirring to pH 4. The resulting solid was collected by filtration providing 1.63 g of Intermediate R. The product was analyzed by chiral SFC (UV detection) using isocratic method (mobile phase: 25% MeOH with 0.1% DMEA, supercritical CO2) on ChiralPak AD-H, 10×250 mm, 5 mum particle size, giving an enantiomeric purity of >95%, Rt 3.88 min (isomer 1) and 4.79 min (isomer 2). 1H NMR (400 MHz, CDCl3) delta ppm 1.37 (ddd, J=8.20, 6.64, 4.69 Hz, 1H), 1.67 (ddd, J=9.28, 5.08, 4.79 Hz, 1H), 1.87 (ddd, J=8.50, 4.69, 4.39 Hz, 1H), 2.48-2.63 (m, 1H), 6.87-7.06 (m, 2H), 7.37-7.46 (m, 2H).
  • 12
  • [ 6142-65-0 ]
  • [ 1240914-03-7 ]
  • 13
  • [ 6142-65-0 ]
  • [ 1241093-84-4 ]
  • 14
  • [ 6142-65-0 ]
  • [ 1240914-95-7 ]
  • 15
  • [ 6142-65-0 ]
  • [ 1240914-98-0 ]
  • 16
  • [ 6142-65-0 ]
  • [ 1240914-90-2 ]
  • 17
  • [ 6142-65-0 ]
  • [ 1240914-92-4 ]
  • 19
  • [ 6142-65-0 ]
  • (±)-trans-O-tert-butyl-N-(2-(4-bromophenyl)cyclopropyl)carbamate [ No CAS ]
  • 20
  • [ 6142-65-0 ]
  • (trans)-2-(4-bromophenyl)cyclopropanecarbonyl azide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Ethyl chloro formate (1.9 mL) was added to a solution of (tra«s)-2-(4-bromophenyl) cyclopropanecarboxylic acid (Intermediate J, 4 g, 0.0165 mol) and Et3N (2.51 mL, 0.0199 mol) in acetone (60 mL) at -20 C, stirred at same temperature for 1 h, then a solution of NaN3 (1.3 g, 0.0199 mol) in water (5 mL), was added and stirred for 30 mins at rt. After completion of reaction, checked by TLC, the solvent was evaporated and crude residue was dissolved in ethyl acetate (100 mL), washed with water (40 mL), dried over anhydrous Na2S04, filtered and evaporated to get (irans)-2-(4-bromophenyl)cyclopropanecarbonyl azide (4 g). The crude residue is carried to next step without further purification.
Intermediate Q: (Trans)-2-(4-bromophenyEthyl chloroformate (1.9 mL) was added to a solution of (frans)-2-(4-bromophenyl) cyclopropanecarboxylic acid (Intermediate P, 4 g, 0.0165 mol) and Et3N (2.51 mL, 0.0199 mol) in acetone (60 mL) at -20 C, stirred at same temperature for 1 h, then a solution of Na 3 (1.3 g, 0.0199 mol) in water (5 mL), was added and stirred for 30 mins at rt. After completion of reaction, checked by TLC, the solvent was evaporated and crude residue was dissolved in ethyl acetate (100 mL), washed with water (40 mL), dried over anhydrous Na2SC>4, filtered and evaporated to get (frans)-2-(4-bromophenyl)cyclopropanecarbonyl azide (4 g). The crude residue is carried to next step without further purification.
Intermediate Q: (Trans)-2-(4-bromophenyEthyl chloroformate (1.9 mL) was added to a solution of (frans)-2-(4-bromophenyl) cyclopropanecarboxylic acid (Intermediate P, 4 g, 0.0165 mol) and Et3N (2.51 mL, 0.0199 mol) in acetone (60 mL) at -20 C, stirred at same temperature for 1 h, then a solution of Na 3 (1.3 g, 0.0199 mol) in water (5 mL), was added and stirred for 30 mins at rt. After completion of reaction, checked by TLC, the solvent was evaporated and crude residue was dissolved in ethyl acetate (100 mL), washed with water (40 mL), dried over anhydrous Na2SC>4, filtered and evaporated to get (frans)-2-(4-bromophenyl)cyclopropanecarbonyl azide (4 g). The crude residue is carried to next step without further purification.
  • 22
  • [ 6142-65-0 ]
  • tert-butyl ((trans)-2-(3'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)cyclopropyl)carbamate [ No CAS ]
  • 23
  • [ 6142-65-0 ]
  • tert-butyl ((trans)-2-(3'-amino-[1,1'-biphenyl]-4-yl)cyclopropyl)carbamate [ No CAS ]
  • 24
  • [ 6142-65-0 ]
  • tert-butyl ((trans)-2-(3'-(1-methylethylsulfonamido)-[1,1'-biphenyl]-4-yl)cyclopropyl)carbamate [ No CAS ]
  • 25
  • [ 6142-65-0 ]
  • N-(4'-((trans)-2-aminocyclopropyl)-[1,1'-biphenyl]-3-yl)propane-2-sulfonamide hydrochloride [ No CAS ]
  • 26
  • [ 6142-65-0 ]
  • (trans)-2-(4-cyclopropylphenyl)-N-(piperidin-4-ylmethyl)cyclopropanamine hydrochloride [ No CAS ]
  • 27
  • [ 6142-65-0 ]
  • tert-butyl 4-(((tert-butoxycarbonyl)((trans)-2-(4-cyclopropylphenyl)cyclopropyl)amino)methyl)piperidine-1-carboxylate [ No CAS ]
  • 28
  • [ 6142-65-0 ]
  • trans-2-(3'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)cyclopropan-1-amine hydrochloride [ No CAS ]
  • 29
  • [ 6142-65-0 ]
  • tert-butyl 4-((((trans)-2-(4-bromophenyl)cyclopropyl)amino)methyl)piperidine-1-carboxylate [ No CAS ]
  • 30
  • [ 6142-65-0 ]
  • tert-butyl 4-((((trans)-2-(4-bromophenyl)cyclopropyl)(tert-butoxycarbonyl)amino)methyl)piperidine-1-carboxylate [ No CAS ]
  • 31
  • [ 6142-65-0 ]
  • tert-butyl ((trans)-2-(2'-methoxy-5'-(methylsulfonamido)-[1,1'-biphenyl]-4-yl)cyclopropyl)carbamate [ No CAS ]
  • 32
  • [ 6142-65-0 ]
  • N-(4'-((trans)-2-aminocyclopropyl)-6-methoxy-[1,1'-biphenyl]-3-yl)methanesulfonamide hydrochloride [ No CAS ]
  • 33
  • [ 6142-65-0 ]
  • tert-butyl ((trans)-2-(3'-amino-[1,1'-biphenyl]-4-yl)cyclopropyl)(4-((tert-butoxycarbonyl)amino)cyclohexyl)carbamate [ No CAS ]
  • 34
  • [ 6142-65-0 ]
  • tert-butyl (4-((tert-butoxycarbonyl)amino)cyclohexyl)((trans)-2-(4-cyclopropylphenyl)cyclopropyl)carbamate [ No CAS ]
  • 35
  • [ 6142-65-0 ]
  • N1-((trans)-2-(4-cyclopropylphenyl)cyclopropyl)cyclohexane-1,4-diamine hydrochloride [ No CAS ]
  • 36
  • [ 6142-65-0 ]
  • tert-butyl (4-((tert-butoxycarbonyl)amino)cyclohexyl)((trans)-2-(3'-(6-nitropyridine-3-sulfonamido)-[1,1'-biphenyl]-4-yl)cyclopropyl)carbamate [ No CAS ]
  • 37
  • [ 6142-65-0 ]
  • tert-butyl (4-((tert-butoxycarbonyl)amino)cyclohexyl)((trans)-2-(3'-(6-aminopyridine-3-sulfonamido)-[1,1'-biphenyl]-4-yl)cyclopropyl)carbamate [ No CAS ]
  • 38
  • [ 6142-65-0 ]
  • 6-amino-N-(4'-((trans)-2-((4-aminocyclohexyl)amino)cyclopropyl)-[1,1'-biphenyl]-3-yl)pyridine-3-sulfonamide hydrochloride [ No CAS ]
  • 39
  • [ 6142-65-0 ]
  • tert-butyl (4-(((trans)-2-(4-bromophenyl)cyclopropyl)amino)cyclohexyl)carbamate [ No CAS ]
  • 40
  • [ 6142-65-0 ]
  • tert-butyl ((trans)-2-(4-bromophenyl)cyclopropyl)(4-((tert-butoxycarbonyl)amino)cyclohexyl)carbamate [ No CAS ]
  • 41
  • [ 1200-07-3 ]
  • [ 6142-65-0 ]
  • 42
  • [ 6142-65-0 ]
  • C15H21BrN2 [ No CAS ]
  • 43
  • [ 6142-65-0 ]
  • C16H16BrN [ No CAS ]
  • 44
  • [ 6142-65-0 ]
  • C16H16BrNO [ No CAS ]
  • 45
  • [ 6142-65-0 ]
  • C16H17BrN2 [ No CAS ]
  • 46
  • [ 6142-65-0 ]
  • C18H21BrN2 [ No CAS ]
  • 47
  • [ 6142-65-0 ]
  • C15H15BrN2 [ No CAS ]
  • 48
  • [ 6142-65-0 ]
  • C16H22BrN3O [ No CAS ]
  • 49
  • [ 6142-65-0 ]
  • [ 90561-75-4 ]
  • 50
  • [ 6142-65-0 ]
  • C21H30BrN3O3 [ No CAS ]
  • 52
  • [ 6142-65-0 ]
  • (1S,2S)-2-(4-(3-methyl-1-(pyridin-2-yl)-1H-indazol-6-yl)phenyl)cyclopropanecarboxylic acid [ No CAS ]
  • 53
  • [ 6142-65-0 ]
  • (1R,2R)-2-(4-(3-methyl-1-(pyridin-2-yl)-1H-indazol-6-yl)phenyl)cyclopropanecarboxylic acid [ No CAS ]
  • 54
  • [ 6142-65-0 ]
  • (1S,2S)-2-(4-(3-methyl-1-p-tolyl-1H-pyrazolo[4,3-c]pyridin-6-yl)phenyl)cyclopropanecarboxylicacid [ No CAS ]
  • 55
  • [ 6142-65-0 ]
  • (S)-3-((1S,2S)-2-(4-bromophenyl)cyclopropanecarbonyl)-4-isopropyloxazolidin-2-one [ No CAS ]
  • 56
  • [ 6142-65-0 ]
  • (S)-3-((1R,2R)-2-(4-bromophenyl)cyclopropanecarbonyl)-4-isopropyloxazolidin-2-one [ No CAS ]
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