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Methyl 3-cyclopropylbenzoate
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[ CAS No. 148438-02-2 ] {[proInfo.proName]}

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Chemical Structure| 148438-02-2
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CAS No. :148438-02-2 MDL No. :MFCD06802403
Formula : C11H12O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 176.21 Pubchem ID :-
Synonyms :

Safety of [ 148438-02-2 ]

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Application In Synthesis of [ 148438-02-2 ]

* 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 [ 148438-02-2 ]

[ 148438-02-2 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 38383-50-5 ]
  • [ 148438-02-2 ]
YieldReaction ConditionsOperation in experiment
94% Stage #1: diiodomethane With diethylzinc; trifluoroacetic acid In hexane; dichloromethane at 0℃; for 0.666667h; Stage #2: methyl 3-ethenylbenzoate In hexane; dichloromethane at 0 - 25℃; for 3h; Stage #3: With ammonium chloride In hexane; dichloromethane; water 235 To a 100 ml round bottom flask charged with a magnetic stir bar and DCM (20 ml) was added 12.3 ml of diethyl zinc (IM in hexanes). The reaction mixture was cooled to 0 0C and trifluoroacetic acid (1.40 g, 12.3 mmol) was added dropwise via syringe. The reaction was stirred at this temperature for 20 mins followed by the addition of CH2I2 (3.30 g, 12.3 mmol). The reaction mixture was stirred for 20 mins before methyl 3-vinylbenzoate (1.00 g, 6.16 mmol) was added. The reaction was then allowed to warm to 25 °C with stirring for 3 h. before being quenched by the addition of ~50 ml of saturated aqueous NH4Cl. The mixture was poured into a sepratory funnel and the aqueous phase was further extracted with DCM (3 X 50 ml). The combined organic extract was dried with MgSO4 and concentrated in vacuo to yield the crude reaction product which was purified on 120 g SiO2 using hexanes-EtOAc 10:1 as eluent giving 1.01 g of the title compound as a colourless oil (94 %); m/z 111.
94% Stage #1: diiodomethane With diethylzinc; trifluoroacetic acid In hexanes; dichloromethane at 0℃; for 0.666667h; Stage #2: methyl 3-ethenylbenzoate In hexanes; dichloromethane at 0℃; for 3h; 32 Method 32; S-Cyclopropylbenzoic acid; To a solution of diethyl zinc (12.3 ml, IM in hexanes) in DCM (20 ml) at 0 0C was added dropwise via syringe trifluoroacetic acid (1.40 g, 12.3 mmol), and after 20 minutes stirring, diiodomethane (3.30 g, 12.3 mmol). After 20 minutes, methyl 3-vinylbenzoate (1.00 g, 6.16 mmol) was added, and the cooling bath removed. After 3 hours, the reaction was quenched by the addition of saturated NH4Cl solution (50 ml). The aqueous phase was extracted with DCM (3 x 50 ml), and the combined organic extract dried (MgSO4) and concentrated in vacuo to yield the crude reaction product which was purified by column chromatography (hexanes/EtOAc 10:1) to give 1.01 g (94 %) methyl 3-cyclopropylbenzoate as a colourless oil; m/z: 111.
Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2006/24834, 2006, A1 Location in patent: Page/Page column 97
[2]Current Patent Assignee: ASTRAZENECA PLC; DAKIN; COOK DON - WO2007/71955, 2007, A1 Location in patent: Page/Page column 55
  • 2
  • [ 1065010-87-8 ]
  • [ 2905-65-9 ]
  • [ 148438-02-2 ]
Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 7481 - 7485
  • 3
  • [ 75-11-6 ]
  • [ 38383-50-5 ]
  • [ 148438-02-2 ]
YieldReaction ConditionsOperation in experiment
94% Stage #1: diiodomethane With diethylzinc; trifluoroacetic acid In hexanes; dichloromethane at 0℃; for 0.666667h; Stage #2: methyl 3-ethenylbenzoate In hexanes; dichloromethane at 0 - 20℃; for 3h; 114 Method 114; Methyl 3-cvclopropylbenzoate; Diethyl zinc (12.3 ml, IM in hexanes) in DCM (20 ml) was cooled to 0 0C and then treated with trifluoroacetic acid (1.40 g, 12.3 mmol) by dropwise addition. The reaction was stirred at 0 0C for 20 min and CH2I2 (3.30 g, 12.3 mmol) was then added. The reaction mixture was stirred for 20 min before methyl 3-vinylbenzoate (1.00 g, 6.16 mmol) was added. The reaction was then allowed to warm to room temperature with stirring for 3 h. before being quenched by the addition of ~50 ml of saturated aqueous NH4Cl. The mixture was poured into a separatory funnel and the aqueous phase was further extracted with DCM. The combined organic extract was dried with MgSO4 (s)and concentrated in vacuo to yield the crude reaction product which was purified on 120 g SiO2 using hexanes/EtOAc 10:1 as eluent giving 1.01 g methyl 3-cyclopropylbenzoate as a colourless oil (94 %); m/z YJl.
Reference： [1]Current Patent Assignee: ASTRAZENECA PLC; DAKIN; LYNE PAUL DERMOT - WO2006/40568, 2006, A1 Location in patent: Page/Page column 77
  • 4
  • [ 1515-75-9 ]
  • [ 6746-94-7 ]
  • [ 148438-02-2 ]
  • [ 148438-01-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: methyl 2,4-pentadienoate; Cyclopropylacetylene With cobalt(II) bromide-[1,2-bis(diphenylphosphino)ethane]; zinc(II) iodide; zinc In dichloromethane at 20℃; Inert atmosphere; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene at 20℃; for 1h; Inert atmosphere;
Reference： [1]Location in patent: experimental part Arndt, Marion; Hilt, Gerhard; Khlebnikov, Alexander F.; Kozhushkov, Sergei I.; De Meijere, Armin [European Journal of Organic Chemistry, 2012, # 16, p. 3112 - 3121]
  • 5
  • [ 618-89-3 ]
  • [ 411235-57-9 ]
  • [ 148438-02-2 ]
YieldReaction ConditionsOperation in experiment
89% With potassium phosphate; palladium diacetate; tricyclohexylphosphine; In water; toluene; at 100℃; for 3h;Inert atmosphere; Step 1 : To a stirred solution of <strong>[618-89-3]methyl 3-bromobenzoate</strong> (3.0 g, 13.950 mmol, 1.0 equiv) in toluene (24 mL) and water (6 mL) (4: 1) was added cyclopropyl boronic acid (1.79 g, 20.900 mmol, 1.5 equiv), potassium phosphate (5.92 g, 27.900 mmol, 2.0 equiv) and tricyclohexylphosphine (0.39 g, 1.390 mmol, 0.1 equiv) at one portion and degassed with Ar gas for 5 min. Pd(OAc)2 (0.15 g, 0.69 mmol, 0.05 equiv), was added and the reaction mixture was stirred for 3 h at 100 C. After completion of the reaction, the reaction was cooled to room temperature, quenched with water and extracted with ethyl acetate (2 χ 100 mL). The organics were combined and washed with brine solution (60 mL) and dried over Na2S04, filtered, and concentrated under reduced pressure to afford the crude product. The crude product was purified by using flash chromatography with 100 - 200 silica gel (24 g column) & using 5% EtOAc in n-Hexane as mobile phase to afford the titled product methyl 3- cyclopropylbenzoate as oily liquid (2.2 g, 89.0 %). LC-MS (ES) m/z = 177.1 [M-H]+. H NMR (400 MHz, DMSO-cfe) δ ppm 0.64 - 0.75 (m, 2 H), 0.96 - 1.04 (m, 2 H), 1.97 - 2.31 (m, 1 H), 3.83 (s, 3 H), 7.33 (d, J = 7.2 Hz, 1 H), 7.38 (t, J = 7.6 Hz, 1 H), 7.64 (s, 1 H), 7.71 (d, J = 7.6 Hz, 1 H).
Reference： [1]Patent: WO2017/46739,2017,A1 .Location in patent: Page/Page column 55

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