[ CAS No. 15823-04-8 ] {[proInfo.proName]}

Name: 15823-04-8|Methyl 3-(4-methoxyphenyl)propanoate|98%
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CAS No. :	15823-04-8	MDL No. :	MFCD01923356
Formula :	C₁₁H₁₄O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AKQLYAFBUYHFCK-UHFFFAOYSA-N
M.W :	194.23	Pubchem ID :	300018
Synonyms :		Chemical Name :	Methyl 3-(4-methoxyphenyl)propanoate

Safety of [ 15823-04-8 ]

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
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Application In Synthesis of [ 15823-04-8 ]

* 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.

Upstream synthesis route of [ 15823-04-8 ]
Downstream synthetic route of [ 15823-04-8 ]

[ 15823-04-8 ] Synthesis Path-Upstream 1~4

1
[ 15823-04-8 ]
[ 13623-25-1 ]

Reference： [1] Synthetic Communications, 1991, vol. 21, # 21, p. 2231 - 2256

2
[ 15823-04-8 ]
[ 1929-29-9 ]

Reference： [1] Synthetic Communications, 1991, vol. 21, # 21, p. 2231 - 2256
[2] Chemische Berichte, 1874, vol. 7, p. 1736[3] Gazzetta Chimica Italiana, 1875, vol. 5, p. 6
[4] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1900, vol. 131, p. 43[5] Annales de Chimie (Cachan, France), 1902, vol. <7> 25, p. 507,537
[6] Journal of Organic Chemistry, 2000, vol. 65, # 13, p. 4179 - 4184
[7] Tetrahedron, 2010, vol. 66, # 14, p. 2633 - 2641

3
[ 104-92-7 ]
[ 292638-85-8 ]
[ 1929-29-9 ]
[ 15823-04-8 ]

Reference： [1] Advanced Synthesis and Catalysis, 2008, vol. 350, # 16, p. 2544 - 2550

4
[ 15823-04-8 ]
[ 4654-08-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 9, p. 2771 - 2782

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Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: 3-(4-methoxyphenyl)propanoic acid With 1H-imidazole; iodine; tris-(o-tolyl)phosphine In dichloromethane at 20℃; for 0.0833333h; Stage #2: methanol In dichloromethane at 20℃;
97%	With sulfuric acid at 20℃;
94.2%	With thionyl chloride at 20℃; for 1h; Cooling with ice;	B-14.1 Synthesis of methyl 3-(4-methoxyphenyl)propanoate To a stuffed solution of thionyl chloride (3.0 ml, 41.62 mmol) in MeOH (30 ml) at cooling with dry ice /methanol bath to rt was added 3-(4-methoxyphenyl)propanoic acid (5 g, 27.74 mmol) after stuffing at rt for 1 h. The solvent was evaporated under reduced pressure, diluted with ethyl acetate and washed with aqueous saturated sodium bicarbonate and brine, then dried over sodium sulphate. The solvent was removed under reduced pressure and the resulting crude was purified by column chromatography, eluted at 2% ethyl acetate in hexane to get the title product (94.2%). LCMS: mlz=195.2 [M+1]. ‘H-NMR (DMSO, 400 MHz) & 7.14-7.12 (dd, 2H 1=8.4Hz), 6.84-6.82 (dd, 1=8.4Hz, 2H), 3.71 (s, 3H), 3.57 (s, 3H), 2.78 (t, 2H), 2.58-2.56 (t, 2H).

90.7%	With thionyl chloride at 20℃; for 3h;	8 3.2.6. General procedure for preparation of 3-(substituted-phenyl)-propionic acid methyl ester General procedure: A mixture of substituted dihydrocinnamic acid (2a-e, 0.133 mol) inmethanol (350 mL) was treated slowly with thionyl chloride (20 mL,0.275 mol) drop wise during 1 h. After completion of addition, the reactionmixture was stirred for another 2 h at rt. After completion ofreaction, which was monitored by TLC hexane/ethyl acetate (8:2), thereaction mixture was poured into water (200 mL), extract with ethylacetate (2×400 mL). The extract was washed with water, brine solution,dried over Na2SO4 and concentrated. The crude compound wassubjected to column chromatography on silica gel using hexane/ethylacetate mixtures. The fractions were monitored and the fractions elutedwith ethyl acetate in hexane, 3%/97% (v/v) were combined and concentratedto obtained 3-(substituted phenyl)-propionic acid methyl esters(3a-e) as oily compounds with yields in the range of 87-90%.
89%	With sulfuric acid for 3.5h; Reflux; Inert atmosphere;
	With sulfuric acid
	With toluene-4-sulfonic acid In various solvent(s) Heating;
	With sulfuric acid
	With sulfuric acid Reflux;
	With sulfuric acid Reflux;
	With sulfuric acid Reflux;
	With sulfuric acid for 18h; Reflux;
	With sulfuric acid at 20℃; for 3.08333h; Reflux;

Yield	Reaction Conditions	Operation in experiment
94%	With potassium hydroxide; water In methanol at 25℃; for 2h;
	With alkaline solution
	With sodium hydroxide In methanol; water for 3h; Heating;

Yield	Reaction Conditions	Operation in experiment
93%	With hydrazine hydrate at 110 - 120℃;
88%	With hydrazine hydrate In methanol at 20℃;
85%	With hydrazine hydrate In methanol Reflux;

[ CAS No. 15823-04-8 ] {[proInfo.proName]}

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[ 15823-04-8 ] Synthesis Path-Upstream 1~4

[ 15823-04-8 ] Synthesis Path-Downstream 1~88

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	With hydrazine hydrate
	With hydrazine hydrate In methanol Reflux;
	With hydrazine hydrate In ethanol for 10h; Reflux;	4.2.1. 2-(4-Methyoxyphenethyl)-1,3,4-oxadiazole Methyl-3-(4-methyoxyphenyl)-propanoate (2.91 g, 15 mmol), 80% hydrazine monohydrate (4.69 g, 75 mmol), 15 ml ethanol were placed in a 50 ml reaction flask equipped with a reflux condenser, and the mixture was heated to reflux for 10 h, the resulting mixture was allowed to cool to room temperature and evaporated in vacuo. The residue was filtered and rinsed with hexane, the product, 3-(4-methoxyphenyl)propanehydrazide, was used in the next step without further purification.
	With hydrazine hydrate In methanol Reflux;
	With hydrazine hydrate In methanol Reflux;

Yield	Reaction Conditions	Operation in experiment
99%	With hydrogen In ethanol at 25℃; for 1h;
99%	With hydrogen In methanol for 2h;	1.4 4) Synthesis of methyl 3-(4-methoxyphenyl)propanoate (shown in FIG. 5); [0065] Methyl-4-methoxycinnamate (11.7g, 61 mmol) was dissolved in 300 mL of methanol. Palladium (5% on activated carbon powder; 1.1 g) was added slowly under strong argon stream. Hydrogen gas was bubbled in and the reaction mixture was stirred vigorously for 2 hours. The solid was filtered off and the filtrates were dried over sodium sulfate. The solvent was evaporated under reduced pressure to obtain methyl 3-(4-methoxyphenyl)proρanoate [15823-04-8] (11.7 g, 99%).
61%	With methanol; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate at 20℃; for 16h; Inert atmosphere; Irradiation; Sealed tube;

	With palladium; acetic acid at 55℃; Hydrogenation;
	With hydrogen In methanol for 0.5h; Ambient temperature;
	With hydrogen In tetrahydrofuran

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate In N,N-dimethyl-formamide	67.1 (1) (1) Ethyl (S)-3-(4-aminophenyl)-2-[3-(4-methoxyphenyl)propionylamino]propionate 3-(4-Hydroxyphenyl)propionic acid (1.36 g, 8.18 mmol) and methyl iodide (1.20 ml, 19.3 mmol) were dissolved in N,N-dimethylformamide (20 ml) and potassium carbonate (3.40 g, 24.6 mmol) was added. The mixture was stirred at 50°-60° C. for 4 hours and at room temperature for 14 hours. The reaction mixture was filtrated and the filtrate was added to saturated brine (1 00 ml) and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate. After filtration, low boiling matters were distilled away from the filtrate under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to give 1.35 g of methyl 3-(4-methoxyphenyl)propionate as a colorless solid (85%).
	With methanol; sodium hydroxide at 120℃; im Druckrohr;
	With potassium carbonate Inert atmosphere;

12 g	With potassium carbonate In N,N-dimethyl-formamide at 20℃;	1 Step 1: Synthesis of 3-(4-Methoxy-phenyl)-propionic acid methyl ester (2) Step 1: Synthesis of 3-(4-Methoxy-phenyl)-propionic acid methyl ester (2)To a suspension of 1 (10.0 g, 60 mmol) and K2003 (21.0 g, 150 mmol) in DMF was added CH3I (26 g, 180 mmol ). The mixture was stirred at rt for overnight. EA (500 m) was added. The mixture was washed with water (150 ml x 2) and brine (100 ml). The organic layer was dried over Na2504, filtered and concentrated to afford 2 as a light yellow oil (12.0 g).
12 g	With potassium carbonate In N,N-dimethyl-formamide at 20℃;	1 Step 1 : Synthesis of 3-(4-Methoxy-phenyl)-propionic acid methyl ester (2) Step 1 : Synthesis of 3-(4-Methoxy-phenyl)-propionic acid methyl ester (2) To a suspension of 1 (10.0 g, 60 mmol) and K2CO3 (21 .0 g, 150 mmol) in DMF was added CH3I (26 g, 180 mmol ). The mixture was stirred at rt for overnight. EA (500 m) was added. The mixture was washed with water (150 ml x 2) and brine (100 ml). The organic layer was dried over Na2SO4, filtered and concentrated to afford 2 as a light yellow oil (12.0 g).

Yield	Reaction Conditions	Operation in experiment
100%	With diisobutylaluminium hydride In tetrahydrofuran at -78℃; for 2.5h; Inert atmosphere;
99%	With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;
95%	With lithium aluminium tetrahydride In diethyl ether

93%	With 5 wt% Re/TiO2; hydrogen In octane at 180℃; for 24h; Autoclave; chemoselective reaction;
90%	With isopropyl alcohol In hexane at 0 - 20℃; for 0.25h; Inert atmosphere;
77.2%	With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2.5h;	14 3.2.12. General procedure for preparation of 3-(substituted-phenyl)-propan-1-ol (4a-e) General procedure: A mixture of Lithium aluminum hydride (9.5 g, 0.250 mol), dry THF(250 mL), to it add substituted dihydrocinnamic acid methyl ester (3ae,0.127 mol), in THF (50 mL) was added slowly drop wise during30 min. After completion of addition the reaction mixture was stirredfor 2 h at rt, after completion of reaction as monitored by TLC hexane/ethyl acetate (8:2), the reaction mixture was poured in water (200 mL),acidified with 5 N HCl, extract with chloroform (2×400 mL), extractwas wash with water, brine solution, dried over Na2SO4 and concentrated.The crude residue was subjected to column chromatographyon silica gel, column was eluted with hexane/ethyl acetate mixtures,pure compound was eluted in ethyl acetate in hexane, 10%/90% (v/v)which was monitored by TLC, pure fractions were combined and concentratedto obtained 3-(substituted phenyl)- propan-1-ol as oily compoundswith yields of 73-77%.
	With lithium aluminium tetrahydride In diethyl ether Heating;
	With lithium borohydride In diethyl ether; toluene for 0.25h; Heating;
	With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Heating;
	With lithium aluminium tetrahydride

Yield	Reaction Conditions	Operation in experiment
97%	With aluminium trichloride In nitrobenzene at 0℃; for 1h;
	With aluminium trichloride

Yield	Reaction Conditions	Operation in experiment
70%	With bis(cyclopentadienyl)titanium dichloride; manganese; chloro-trimethyl-silane; triphenylphosphine; nickel dichloride In tetrahydrofuran at 50℃; for 16h; Inert atmosphere;
62%	With pyridine; nickel(II) dichloro tris(triphenylphoshpine); zinc In acetonitrile at 65℃; for 4h;
62%	With pyridine; bis(triphenylphosphine)nickel(II) chloride; zinc In acetonitrile at 65℃; for 4h;

Yield	Reaction Conditions	Operation in experiment
98%	With hydrazine hydrate In ethanol for 5.5h; Reflux;
96%	With magnesium In methanol at 10℃; for 2.5h;
86%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; tetrahydroxydiboron; water; triethylamine In tetrahydrofuran at 30℃; for 12h; Schlenk technique; Inert atmosphere;

84%	With 2-(Aminomethyl)pyridine; bromopentacarbonylmanganese(I); potassium <i>tert</i>-butylate; hydrogen In 1,4-dioxane at 100℃; for 20h; Autoclave; chemoselective reaction;	4.3. Representative procedure for the catalytic hydrogenation reactions General procedure: A 4 ml glass vial was sequentially charged with solid [Mn(CO)5Br](0.015 0.030 mmol), the substrate (0.5 mmol), 2-picolylamine(0.015 0.030 mmol), and a magnetic stirring bar. The reaction componentswere then dissolved in THF (2 ml) or 1,4-dioxane (2 ml)whereupon the resulting yellow solution was then gently stirred(200 rpm) for a period of 5 min. Whilst stirring, the glass vial was sealed with the septum cap. Hereafter, solid t-BuOK (0.015 0.030 mmol) was added to the reaction mixture upon which the reaction vessel was again sealed with a septum cap which was then penetrated with a needle.Notably, the base addition was carried out without stirring. After that,the glass vial was placed in a drilled aluminum liner which was promptly transferred into the 300 ml autoclave. Once tightly sealed, the latter was purged five times with H2 (20 bar per cycle) before being pressurized to the desired value. The autoclave was then placed on a pre-heated stirring plate and heated up to the required reaction temperature. On completion of the hydrogenation reaction, the autoclave was allowed to reach room temperature. Afterwards, the remaining gas was slowlyreleased upon which the reaction mixture was degassed through brieflystirring on air. Finally, n-dodecane (12 mg) or n-hexadecane (20 mg)were added and an aliquot of 30 μl was taken from the solution, mixedwith acetone (1 ml) whereupon the resulting solution was analyzed byGC.
82%	With hydrazine hydrate In acetonitrile at 20℃; for 24h; Irradiation;
	With hydrogen
99 %Spectr.	With borane-ammonia complex; 2-H-1,3-di-tert-butyl-2,3-dihydro-1H-1,3,2-diazaphosphole In [D₃]acetonitrile at 50℃; for 8h; regioselective reaction;

Yield	Reaction Conditions	Operation in experiment
57%	Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #2: methyl 3-(4-methoxyphenyl)propionate In tetrahydrofuran; hexane at -78 - 20℃; for 0.583333h; Inert atmosphere;	Dimethyl (4-(4-methoxyphenyl)-2-oxobutyl)phosphonate 7d n-Butyllithium (2.5 M in hexanes, 22.0 mL, 55.1 mmol) was added slowly to a solution of dimethyl methylphosphonate (6.00 mL, 55.1 mmol) in anhydrous THF (100 mL) at -78°C under argon. The reaction mixture was stirred at -78°C for 1h, then a solution methyl 3-(4-methoxyphenyl)propanoate14 (10.7g, 55.1mmol) in THF (50mL) was added dropwise. The mixture was stirred at -78°C for 5 min, then at rt for 30 min, after which the reaction was quenched with saturated aqueous NH4Cl (100 mL) and extracted with Et2O (3×100 mL). The combined organics were dried (Na2SO4) and concentrated to afford a pale yellow oil (15.8 g). The crude product was purified by chromatography (silica gel, 100% EtOAc) to afford the title compound (9.00g, 57%) as a colorless oil. IR 2956, 1712cm-1; δH (400MHz, CDCl3) 7.23-7.06 (m, 2H), 6.93-6.76 (m, 2H), 3.80 (s, 3H), 3.79 (s, 3H), 3.76 (s, 3H), 3.09 (d, J=22.7Hz, 2H), 2.98-2.84 (m, 4H); δC (100MHz, CDCl3) 201.1 (C, d, J=6.1Hz), 158.0 (C), 132.6 (C), 129.3 (CH), 113.9 (CH), 55.3 (CH3), 53.1 (CH3), 53.0 (CH3), 45.8 (CH2), 41.5 (CH2, d, J=128Hz), 28.6 (CH2); m/z (ESI+) found [M+H]+ 287.1049. C13H20O5P+ requires 287.1043.
	Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran at 0℃; Stage #2: methyl 3-(4-methoxyphenyl)propionate In tetrahydrofuran

Yield	Reaction Conditions	Operation in experiment
97%	With bromine In dichloromethane at 0℃; for 2h;	methyl 3-(3-bromo-4-methoxyphenyl)propanoate (2a) Bromine (2.0 mL, 49.0 mmol) was slowly added to a solution of 1a (10 g, 51.5 mmol) in CH2Cl2 (80 mL) at 0 °C. The reaction proceeded for 2 hr and was quenched with ice water. The organic fraction was extracted with CH2Cl2, washed with sat. aq. NaHCO3 and brine, and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure and the product 2a was obtained as a thick oily material (14 g, 97%).
92%	With aluminium trichloride; bromine In dichloromethane at 0℃; for 0.333333h;
	With bromine In dichloromethane at -30 - -15℃; Inert atmosphere;	In a 1000 mL flask under nitrogen, ester 1 (35 g, 180 mol) was dissolved in 350 mL CH2CI2 and cooled to -30°C. Bromine (9.93 mL) was added dropwise without an exotherm. The reaction mixture was warmed slowly to - 15°C. The reaction was complete by LC. The product was diluted with 300 mL of 7% NaHC03 solution. Sodium thiosulfate (pentahydrate) solid (4.5 g) was added to decolorize. The layers were separated, and the organic layer was dried with MgSO.}. The solvent was removed by evaporation. The product was used directly in the next step.

16.8 g	With aluminum (III) chloride; bromine In dichloromethane at 0℃; for 0.333333h;	2 Step 2: Synthesis of 3-(3-Bromo-4-methoxy-phenyl)-propionic acid methyl ester (3) Step 2: Synthesis of 3-(3-Bromo-4-methoxy-phenyl)-propionic acid methyl ester (3) To a solution of 2 (12.0 g, 61 .9 mmol) in DCM (150 ml) was added AICI3 (8.3 g,61 .9 mmol) at ice/salt bath. Then Br2 (9.9 g, 61 .9 mmol) was added dropwise. The mixture was stirred at 0 °C for 20 minutes. The reaction mixture was poured intoice/water (200 ml) and extracted with DCM (150 ml x 3). The combined organic layer was washed with Na25203 (aq, 150 ml) and brine (150 ml), dried over Na2504, filtered and concentrated to afford 3 as a light yellow oil (16.8 g).
16.8 g	With aluminum (III) chloride; bromine In dichloromethane at 0℃; for 0.333333h;	2 Step 2: Synthesis of 3-(3-Bromo-4-methoxy-phenyl)-propionic acid methyl ester (3) Step 2: Synthesis of 3-(3-Bromo-4-methoxy-phenyl)-propionic acid methyl ester (3) To a solution of 2 (12.0 g, 61 .9 mmol) in DCM (150 ml) was added AICI3 (8.3 g, 61 .9 mmol) at ice/salt bath. Then Br2 (9.9 g, 61 .9 mmol) was added dropwise. The mixture was stirred at 0 °C for 20 minutes. The reaction mixture was poured into ice/water (200 ml) and extracted with DCM (150 ml x 3). The combined organic layer was washed with Na2S2O3 (aq, 150 ml) and brine (150 ml), dried over Na2SO4, filtered and concentrated to afford 3 as a light yellow oil (16.8 g).

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate In acetone Heating;
95%	With potassium carbonate In acetone for 48h; Reflux;

Yield	Reaction Conditions	Operation in experiment
90%	With diisobutylaluminium hydride In hexane; dichloromethane at -78℃; for 1.16667h;	3-(4-Methoxyphenyl)propanal (S2). A reported procedure1 was adapted for the synthesis of aldehyde S2. A solution of methyl 3-(4-methoxyphenyl)propanoate (S1, 1.9 g, 9.9 mmol) in CH2Cl2 (50 mL) was cooled to -78 °C. DIBAL-H (10 mL, 1 M in hexanes, 10 mmol) was added dropwise over 10 min. After 1 h, saturated aqueous NH4Cl (50 mL) was added, and mixture was warmed to room temperature. The product was extracted with CH2Cl2 (5 x 50 mL). The combined organic layers were washed with brine (100 mL) and concentrated in vacuo. Purification by flash chromatography (5:95 - 20:80 Et2O:hexanes) yielded S2 as a colorless oil (1.1 g, 90%). The spectroscopic data are consistent with the data reported:1
87%	With diisobutylaluminium hydride In dichloromethane at -80℃;
78%	With diisobutylaluminium hydride In dichloromethane; toluene at -78℃; Inert atmosphere;

	Multi-step reaction with 2 steps 1: LiAlH₄ 2: PCC
	Multi-step reaction with 2 steps 1.1: diisobutylaluminium hydride / tetrahydrofuran / 2.5 h / -78 °C / Inert atmosphere 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 2.2: 0.33 h / 20 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 2.5 h / 20 °C 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide
	Stage #1: methyl 3-(4-methoxyphenyl)propionate With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 5h; Reflux; Stage #2: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In ethyl acetate for 6h; Reflux;
	With diisobutylaluminium hydride In toluene; pentane at -78℃; for 1h; Inert atmosphere;

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: H₂ / Pd/C 2: H₂SO₄
	Multi-step reaction with 2 steps 1: H₂ / 5 percent Pd/C / ethyl acetate 2: MeOH
	Multi-step reaction with 2 steps 1: zinc amalgam; hydrogenchloride / tetrahydrofuran; water 2: thionyl chloride / 3 h / 20 °C

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 94 percent / tetrahydrofuran / 4 h / Heating 2: 99 percent / H₂ / 10percent Pd/C / ethanol / 1 h / 25 °C / 2327.2 Torr
	Multi-step reaction with 2 steps 1: dichloromethane / 72 h 2: hydrazine hydrate / acetonitrile / 24 h / 20 °C / Irradiation
	Multi-step reaction with 2 steps 1: piperidine; pyridine / Reflux 2: (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; methanol / 16 h / 20 °C / Inert atmosphere; Irradiation; Sealed tube

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: iodine; silver sulfate / methanol / 1 h / 20 °C 2: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; dimethyl sulfoxide / 17 h / 50 - 80 °C / Inert atmosphere 3: potassium carbonate / dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; tetrahydrofuran / 16 h / 20 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1.1: bromine / dichloromethane / -30 - -15 °C / Inert atmosphere 2.1: potassium acetate / cyclopentylmethyl ether / 1 h / Inert atmosphere 2.2: 22 h / 80 °C / Inert atmosphere 3.1: potassium carbonate / dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; tetrahydrofuran / 16 h / 20 °C / Inert atmosphere
	Multi-step reaction with 5 steps 1.1: bromine / dichloromethane / -30 - -15 °C / Inert atmosphere 2.1: potassium acetate / cyclopentylmethyl ether / 1 h / Inert atmosphere 2.2: 22 h / 80 °C / Inert atmosphere 3.1: potassium carbonate / dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; tetrahydrofuran / 1 h / 45 °C / Inert atmosphere 4.1: N,N-dimethyl-formamide; thionyl chloride / 20 °C / Cooling 5.1: sodium hexamethyldisilazane / N,N-dimethyl-formamide / -20 - -15 °C 5.2: -15 - 20 °C

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: iodine; silver sulfate / methanol / 1 h / 20 °C 2: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; dimethyl sulfoxide / 17 h / 50 - 80 °C / Inert atmosphere 3: potassium carbonate / dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; tetrahydrofuran / 16 h / 20 °C / Inert atmosphere 4: water; lithium hydroxide / 1,4-dioxane / 3 h / 20 °C
	Multi-step reaction with 4 steps 1.1: bromine / dichloromethane / -30 - -15 °C / Inert atmosphere 2.1: potassium acetate / cyclopentylmethyl ether / 1 h / Inert atmosphere 2.2: 22 h / 80 °C / Inert atmosphere 3.1: potassium carbonate / dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; tetrahydrofuran / 16 h / 20 °C / Inert atmosphere 4.1: water; lithium hydroxide / 1,4-dioxane / 3 h / 20 °C
	Multi-step reaction with 6 steps 1.1: bromine / dichloromethane / -30 - -15 °C / Inert atmosphere 2.1: potassium acetate / cyclopentylmethyl ether / 1 h / Inert atmosphere 2.2: 22 h / 80 °C / Inert atmosphere 3.1: potassium carbonate / dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; tetrahydrofuran / 1 h / 45 °C / Inert atmosphere 4.1: N,N-dimethyl-formamide; thionyl chloride / 20 °C / Cooling 5.1: sodium hexamethyldisilazane / N,N-dimethyl-formamide / -20 - -15 °C 5.2: -15 - 20 °C 6.1: water; lithium hydroxide / 1,4-dioxane / 3 h / 20 °C

Yield	Reaction Conditions	Operation in experiment
	With iodine; silver sulfate In methanol at 20℃; for 1h;	2.1 To a solution of methyl 3 -(4-methoxyphenyl)propanoate (100 g, 515 mmol) inMeOH (2L) was added Ag≥S04 (161 g, 515 mmol) followed by . (131 g, 515 mmol). The reaction was stirred vigorously at room temperature for 1 hour and then the solids were removed by filtration. The filtrate was concentrated and the residue was taken up in EtOAc (4L), and washed with water (1L), saturated aq. NaHSC>3 (1L), and brine (1L). The organic layer was dried over MgS04> filtered, and concentrated. Purification of the residue by flash chromatography on silica gel with 0 to 30% EtOAc/heptanes afforded methyl 3-(3-iodo-4- methoxyphenyl)propanoate. NMR (500 MHz, CDC ) 7.61 (d,J= 2.0 Hz, 1H), 7.14 (dd, J= 8.2, 2.0 Hz, 1H), 6.74 (d, J= 8.5 Hz, lH), 3.85 (s, 3H), 3.67 (s, 3H), 2.85 (t, J= 7.8 Hz, 2H), 2.59 (t,J= 7.8 Hz, 2H).
	With iodine; silver sulfate In methanol at 20℃; for 1h;	2.A To a solution of methyl 3-(4-methoxyphenyl)propanoate (5 g, 25.7 mmol) in MeOH (75 mL) was added Ag2SC>4 (8.03 g, 25.7 mmol) followed by I2 (6,53 g, 25.7 mmol). The reaction was stirred vigorously at room temperature for 1 hour and then the solids were removed by filtration through Celite. The filtrate was concentrated and the residue was taken up in EtOAc (150 mL), and washed with water (50 mL), aq. NaHS03 (2 x 50 mL), and brine (50 mL). The organic layer was dried over Na2S04, filtered, and concentrated. Purification of the reside by flash chromatography on silica gel afforded methyl 3-(3-iodo-4-methoxyphenyl)propanoate. .H NMR (500 MHz, CDC13) 6 7.61 (d, J- 2.0 Hz, 1H), 7.14 (dd, J= 8.2, 2.0 Hz, 1H), 6.74 (d, J = 8.5 Hz, 1H), 3.85 (s, 3H), 3.67 (s, 3H), 2.85 (t, J= 7.8 Hz, 2H)} 2.59 (t, J= 7.8 Hz, 2H).
155 g	With iodine; silver sulfate In methanol at 20℃; for 1h; Inert atmosphere;	1 Step 1 Step 1 A 3-neck 5 L RBF equipped with mechanical stirrer, thermometer, and a nitrogen bubbler, was charged with 3-(4-methoxyphenyl)propionic acid methyl ester (100 g, 515 mmol), silver sulfate (161 g, 515 mmol) and iodine (131 g, 515 mmol) in methanol (2 L). The reaction mixture was stirred vigorously at room temperature for 1 hour. The reaction was filtered through Solka-Floc (ethyl acetate wash). The filtrate was concentrated and the residue was taken up in ethyl acetate (4 L). The organic was washed with water, saturated aq. NaHSO3 (50 mL), and brine (50 mL) before drying over Na2SO4, filtering, and concentrating to dryness. The crude reaction was purified by column chromatography to yield methyl 3-(3-iodo-4-methoxyphenyl)propanoate (155 g, 484 mmol) as a clear oil. MS ESI calc'd. for C11H14IO3 [M+H]+ 321.0. found 321.0.

	With iodine; silver sulfate In methanol at 20℃; for 1h; Inert atmosphere;	Step 1: A 3-neck 5 L RBF equipped with mechanical stirrer, thermometer, and anitrogen bubbler, was charged with 3-( 4-methoxyphenyl)propionic acid methyl ester (1 00 g, 515mmol), silver sulfate (161 g, 515 mmol) and iodine (131 g, 515 mmol) in methanol (2 L). Thereaction mixture was stirred vigorously at room temperature for 1 hour. The reaction was filtered through Solka Floc (ethyl acetate wash). The filtrate was concentrated and the residue was takenup in ethyl acetate (4 L). The organic was washed with water, saturated aq. NaHS03 (50 mL),and brine (50 mL) before drying over Na2S04, filtering, and concentrating to dryness. The crudereaction was purified by column chromatography to yield methyl 3-(3-iodo-4-methoxyphenyl)propanoate as a clear oil. MS ESI calc'd. for C11H14103 [M + H]+ 321.0, found 321.0
155 g	With iodine; silver sulfate In methanol at 20℃; for 1h; Inert atmosphere;

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: iodine; silver sulfate / methanol / 1 h / 20 °C 2: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; dimethyl sulfoxide / 17 h / 50 - 80 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1.1: bromine / dichloromethane / -30 - -15 °C / Inert atmosphere 2.1: potassium acetate / cyclopentylmethyl ether / 1 h / Inert atmosphere 2.2: 22 h / 80 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: iodine; silver sulfate / methanol / 1 h / 20 °C / Inert atmosphere 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / 1,4-dioxane; dimethyl sulfoxide / 50 - 80 °C / Inert atmosphere

	Multi-step reaction with 2 steps 1: silver sulfate; iodine / methanol / 1 h / 20 °C / Inert atmosphere 2: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; dimethyl sulfoxide / 50 - 80 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: iodine; silver sulfate / methanol / 1 h / 20 °C 2: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; dimethyl sulfoxide / 17 h / 50 - 80 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: iodine; silver sulfate / methanol / 1 h / 20 °C / Inert atmosphere 2: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; dimethyl sulfoxide / 50 - 80 °C / Inert atmosphere

Yield	Reaction Conditions	Operation in experiment
68%	With CAL-B (Candida antarctica lipase B) immobilized on an acrylic resin (Novozyme 435) In tert-butyl methyl ether at 45℃; for 24h; Schlenk technique; Enzymatic reaction;	2. General procedure for the enzyme catalyzed amidation reaction To a solution of 55 mg (1.00 mmol) of propargyl amine (2), in dry MTBE (2 mL) in a screwcapSchlenk vessel, were added 1.5 mmol of the methyl ester 1 (for experimental details seeTable 1) and Novozyme 435 (50 % w/w of corresponding ester substrate used) and thereaction was shaken in an incubating shaker at 45 °C for 4 or 24 h (depending upon the natureof ester used). After the reaction time, the enzyme beads were filtered off and the filtrate wassubjected to column chromatography on silica gel (n-hexane/ethylacetate 1:1 or 2:1) to obtainthe pure product 3.
	With Candida antarctica lipase B In tert-butyl methyl ether at 45℃; for 24h; Schlenk technique; Inert atmosphere; Enzymatic reaction;

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 20 °C / Inert atmosphere 3: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / dichloromethane; water / 8 h / 20 °C / Inert atmosphere 4: 2,6-dimethylpyridine / N,N-dimethyl-formamide / 2 h / 110 °C / Inert atmosphere
	Multi-step reaction with 4 steps 1: tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 20 °C / Inert atmosphere 3: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / dichloromethane; water / 8 h / 20 °C / Inert atmosphere 4: 2,6-dimethylpyridine / N,N-dimethyl-formamide / 2 h / 110 °C / Inert atmosphere

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 60 °C / Inert atmosphere 3: 2,6-dimethylpyridine / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere 4: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / dichloromethane; water / 5 h / 20 °C / Inert atmosphere 5: 2,6-dimethylpyridine / N,N-dimethyl-formamide / 2 h / 110 °C / Inert atmosphere
	Multi-step reaction with 5 steps 1: tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 60 °C / Inert atmosphere 3: 2,6-dimethylpyridine / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere 4: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / dichloromethane; water / 5 h / 20 °C / Inert atmosphere 5: 2,6-dimethylpyridine / N,N-dimethyl-formamide / 2 h / 110 °C / Inert atmosphere

Yield	Reaction Conditions	Operation in experiment
1: 89% 2: 9%	Stage #1: 4-Methoxystyrene; carbon monoxide With hydrogenchloride In water for 20h; Schlenk technique; Inert atmosphere; Stage #2: methanol With diazomethyl-trimethyl-silane In water for 2h; Schlenk technique; Inert atmosphere; Reflux;	Experimental procedure for the synthesis of 2-aryl-propionic acids General procedure: In a 100 mL Schlenk vial 0.75 mol% (11.79 mg) Pd(OAc)2, 3.0 mol% (67.7 mg) NIPCDPP 9 weredissolved in 14 mL dioxane and 0.2 eq (410 μL) hexadecane as internal standard was added. Underargon 2.0 mL of this homogeneous yellow stock solution was transferred to each of six 4 mL vialsequipped with a septum, needle and stirring bar, which are placed in an alloy plate. After 1 mmolof the corresponding aryl bromide and 1.5 eq (208 μL) of NEt3 were added to each vial and a smallsample was withdrawn for GC, the alloy plate was transferred into the 300 mL autoclave. Thesealed autoclave was purged with ethylene several times and pressurized with 10 bar ethylene.Then, the reaction was run at 120 °C for 20 h. Afterwards the autoclave was cooled down to roomtemperature and the gas was carefully released. In the vials a grey precipitate were formed and thesolution was still yellow. After a small sample for GC analyses was withdrawn, 83 μL of 6M HCLwas added carefully. The reaction solution foams. Next, the autoclave was flushed with CO threetimes and the reaction was allowed to run at 40 bar CO. After 20 h, the autoclave was cooled downand the gas was released again. In order to determine the yield by GC, a sample of 100 μL of eachreaction solution was esterified with (trimethylsilyl)diazomethane in the presence of 100 μL MeOH.The products were chromatographed after esterification in 10 mL MeOH and one drop cc H2SO4 (2h refluxing) and characterized by NMR, elemental analysis and mass spectroscopy.
	With 1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; 1,2-bis[di(t-butyl)phosphinomethyl]benzene; bis(dibenzylideneacetone)-palladium⁽⁰⁾ In dichloromethane at 20℃; for 14h; Overall yield = 97 %; Overall yield = 193 mg; regioselective reaction;
	With platinum(II) bis(acetylacetonate); C₂₈H₃₆P₂; toluene-4-sulfonic acid at 120℃; for 20h; Sealed tube; Inert atmosphere; Autoclave; Overall yield = 85 percent;

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