* 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.
Reference：
[1] Russian Journal of Organic Chemistry, 2002, vol. 38, # 12, p. 1769 - 1774
2
[ 42287-90-1 ]
[ 65537-54-4 ]
Yield
Reaction Conditions
Operation in experiment
100%
With borane-THF In tetrahydrofuran at 14℃; for 18 - 22 h; Heating / reflux
To a solution of 3-(3-bromophenyl)propionic acid (10.0 g, 43.7 mmol) in anhydrous THF (150 mL) was added 1.0 M BH3.THF (150 mL, 150 mmol) via addition funnel. After BH3.THF was added, the reaction was refluxed for 18 hrs. The reaction was quenched with water (100 mL) and 1N HCl (300 mL). The solution was saturated with sodium chloride and extracted with ethyl acetate. The organic extract was washed with brine and dried over magnesium sulfate. The organic material was purified by chromatography on silica gel eluting with ethyl acetate in hexane to produce 9.39 g (100percent) of the desired alcohol as a colorless oil. NMR (CDCl3) δ 1.82-1.89 (m, 2H), 2.67 (t, 2H), 3.64 (t, 2H), 7.11 7.15 (m, 1H), 7.29-7.31 (m, 1H), 7.34 (s, 1H).Part A. Preparation of: To a solution of 3-(3-bromophenyl)propionic acid (15.0 g, 65.5 mmol) in anhydrous THF (200 mL) at 5° C. was added, via addition funnel, 1.0 M BH3-THF (200 mL, 200 mmol). The reaction temperature was kept below 14° C. during the addition of the BH3THF. After all the BH3THF was added, the reaction was refluxed for 22 hr and then quenched with water (100 mL) and 1N HCl (300 mL). The solution was saturated with sodium chloride and extracted with ethyl acetate (3.x.300 mL). The organic extract was washed with brine, dried over magnesium sulfate, and concentrated providing 14.4 g (100percent) of crude alcohol as a colorless oil. NMR(CDCl3) δ 1.82-1.89 (m, 2H), 2.67 (t, 2H), 3.64 (t, 2H), 7.11-7.15 (m, 1H), 7.29-7.31 (m, 1H), 7.34 (s, 1H).
98%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 3 h; Stage #2: With sodium hydroxide; water In tetrahydrofuran
Example 36. 3-(3-Bromo-plienvr)-propan-l-oI (23); [0173] 3-(3-Bromo-phenyl)-propionic acid (3.88 g, 16.9 mmol, 1 equiv) was diluted with THF (50 mL) and chilled to O0C. IM LAH solution added slowly so as to not allow internal reaction temperature to climb above 10-15°C. Once LAH addition was complete, reaction allowed to come to room temperature and stir for 3h. Reaction then quenched with sequential addition of water (0.5 mL), 15percent NaOH (0.5 mL) and water again(1.5 mL). This was then filtered and solvents evaporated to provide the product as a pale oil (2.75g, 98percent). Ri = 0.42 (30percent EtOAc/hexanes).
28%
With borane-THF In tetrahydrofuran at 0 - 20℃; Inert atmosphere
Into a 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 3-(3-bromophenyl)propanoic acid (5 g, 21.83 mmol, 1.00 equiv) in THF (50 mL). This was followed by the addition of borane tetrahydrofuran complex solution (1 moL/L, 75 mL, 74.22 mmoL, 3.40 equiv) dropwise with stirring at 0° C. The resulting solution was stirred overnight at room temperature. The reaction mixture was poured into 150 mL of HCl (1 moL/L), extracted with 3×200 mL of DCM, washed with 300 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with DCM/MeOH (10:1). The collected fraction was concentrated to afford 3-(3-bromophenyl)propan-1-ol (1.3 g, 28percent) as colorless oil. 1H-NMR (DMSO, 400 MHz) δ(ppm): 7.41-7.20 (m, 4H), 4.51-4.48 (t, 1H), 3.41-3.34 (m, 2H), 2.67-2.59 (m, 2H), 1.73-1.66 (m, 2H).
9.8 g
With borane-THF In tetrahydrofuran at 0℃; for 17 h; Inert atmosphere; Reflux
To a cooied (ice bath) soiution of 3-(3-bromophenyi)propanoic acid (8.0 g,35 mmoi) in anhydrous THF (100 mL) was added BH3-THF (100 mL, 1.0 M) via addition funnei under a nitrogen atmosphere. The reaction was stirred at 0 °C for 1 h then at refiux for 16 h. The reaction was carefuiiy quenched with HCi (37 mL, 2 M) then concentrated to remove THF. The suspension was diiuted withDCM (300 mL) then fiitered to remove the soiids. The iayers were separatedand the organic phase was washed with water (50 mL) and brine (50 mL) then dried over anhydrous Na2SO4, filtered, and concentrated to give 3-(3-bromophenyl)propan-1-ol (9.8 g, >100percent) as a yellow oil, which was used for next step without further purification.
Reference：
[1] Patent: US2004/10019, 2004, A1, . Location in patent: Page 160; 167
[2] Patent: WO2006/101977, 2006, A2, . Location in patent: Page/Page column 56
[3] Journal of Organic Chemistry, 2010, vol. 75, # 15, p. 5178 - 5194
[4] Angewandte Chemie - International Edition, 2018, vol. 57, # 15, p. 4058 - 4062[5] Angew. Chem., 2018, vol. 130, p. 4122 - 4126,5
[6] Patent: US2016/264518, 2016, A1, . Location in patent: Paragraph 0969; 0970
[7] Patent: US2007/27141, 2007, A1, . Location in patent: Page/Page column 9
[8] Patent: WO2016/147144, 2016, A1, . Location in patent: Page/Page column 113; 114
Reference：
[1] Bulletin de la Societe Chimique de France, 1983, vol. 2, # 3-4, p. 96 - 104
[2] Russian Journal of Organic Chemistry, 2002, vol. 38, # 12, p. 1769 - 1774
5
[ 151583-29-8 ]
[ 42287-90-1 ]
Reference：
[1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 9, p. 2612 - 2621
6
[ 125115-01-7 ]
[ 42287-90-1 ]
Reference：
[1] Russian Journal of Organic Chemistry, 2002, vol. 38, # 12, p. 1769 - 1774
Example 37A: methyl 3-(3-bromophenyl)propanoate j00412j 3-(3-bromophenyl)propanoic acid (1 g, 4.37 mmol) was dissolved in MeOH(17.46 mL). SOC12 (1.593 mL, 21.83 mmol) was added dropwise, and the reactionheated to reflux for 3 h. The reaction was concentrated in vacuo to yield Example 37A (1.08 g, 100percent). 1H NMR (400 MHz, CHLOROFORM-d) ö ppm 7.30 - 7.42 (2 H, m), 7.06 - 7.21 (2 H, m), 3.67 (3 H, s), 2.92 (2 H, t, J=7.78 Hz), 2.62 (2 H, t, J=7.65 Hz).
99%
for 16 h; Reflux
General procedure: In distinct reactors, solutions of the appropriate 3-(3-bromophenyl)-propionic acid or 3-(4-Bromophenyl)-propionic acid in MeOH were prepared and concentrated H2SO4 was added to each reactor. The resulting mixtures were stirred under reflux for 16h. Each crude mixture was reduced under vacuo and the residues were partitioned with dichloromethane(20 mL) and saturated NaHCO3 solution(20 mL). The organic layers of each reaction was dried with Na2SO4, filtered and evaporated. The resulting compounds were used in a further reaction without any further purification.
Reference：
[1] Journal of Organic Chemistry, 2012, vol. 77, # 5, p. 2225 - 2235
[2] Patent: WO2014/201073, 2014, A1, . Location in patent: Paragraph 00412
[3] European Journal of Medicinal Chemistry, 2012, vol. 48, p. 206 - 213
With triethylamine; 1,1'-carbonyldiimidazole; magnesium chloride; In acetonitrile; at 90℃; for 5.5h;
Ethyl 5-(3-bromophenyl)-3-oxopentanoate (Scheme 4, B); To a round bottom flask was added magnesium chloride (10.4 g, 109 mmol), acetonitrile (580 mL), potassium malonate (15.6 g, 92 mmol), and triethlamine (19.5 mL, 140 mmol). Separately, <strong>[42287-90-1]3-(3-bromophenyl)propionic acid</strong> (10 g, 44 mmol) (Scheme 4, A) was dissolved in acetonitrile (200 mL) and to this was added l3l'-carbonyldiimidazole (CDI) (7.8 g, 48 mmol). Both were allowed to stir for approximately 2.5 hours then the <strong>[42287-90-1]3-(3-bromophenyl)propionic acid</strong>/CDI solution was added dropwise to the mixture OfMgCl2, potassium ethyl malonate and Et3N. The reaction was stirred overnight, then was heated at 90 C for 3 h. It was then allowed to cool to room temperature, filtered and rinsed with acetonitrile (3x100 mL). The combined filtrates were concentrated under reduced pressure then partitioned between methylene chloride and water. The product was extracted into the methylene chloride layer which was then washed 10% aqueous citric acid solution, dried over sodium sulfate and concentrated under reduced pressure to give the desired product (9.72 g, 75%). This material was used without purification.
With borane-THF; In tetrahydrofuran; at 14℃; for 18 - 22h;Heating / reflux;
To a solution of <strong>[42287-90-1]3-(3-bromophenyl)propionic acid</strong> (10.0 g, 43.7 mmol) in anhydrous THF (150 mL) was added 1.0 M BH3.THF (150 mL, 150 mmol) via addition funnel. After BH3.THF was added, the reaction was refluxed for 18 hrs. The reaction was quenched with water (100 mL) and 1N HCl (300 mL). The solution was saturated with sodium chloride and extracted with ethyl acetate. The organic extract was washed with brine and dried over magnesium sulfate. The organic material was purified by chromatography on silica gel eluting with ethyl acetate in hexane to produce 9.39 g (100%) of the desired alcohol as a colorless oil. NMR (CDCl3) delta 1.82-1.89 (m, 2H), 2.67 (t, 2H), 3.64 (t, 2H), 7.11 7.15 (m, 1H), 7.29-7.31 (m, 1H), 7.34 (s, 1H).Part A. Preparation of: To a solution of <strong>[42287-90-1]3-(3-bromophenyl)propionic acid</strong> (15.0 g, 65.5 mmol) in anhydrous THF (200 mL) at 5 C. was added, via addition funnel, 1.0 M BH3-THF (200 mL, 200 mmol). The reaction temperature was kept below 14 C. during the addition of the BH3THF. After all the BH3THF was added, the reaction was refluxed for 22 hr and then quenched with water (100 mL) and 1N HCl (300 mL). The solution was saturated with sodium chloride and extracted with ethyl acetate (3×300 mL). The organic extract was washed with brine, dried over magnesium sulfate, and concentrated providing 14.4 g (100%) of crude alcohol as a colorless oil. NMR(CDCl3) delta 1.82-1.89 (m, 2H), 2.67 (t, 2H), 3.64 (t, 2H), 7.11-7.15 (m, 1H), 7.29-7.31 (m, 1H), 7.34 (s, 1H).
98%
Example 36. 3-(3-Bromo-plienvr)-propan-l-oI (23); [0173] 3-(3-Bromo-phenyl)-propionic acid (3.88 g, 16.9 mmol, 1 equiv) was diluted with THF (50 mL) and chilled to O0C. IM LAH solution added slowly so as to not allow internal reaction temperature to climb above 10-15C. Once LAH addition was complete, reaction allowed to come to room temperature and stir for 3h. Reaction then quenched with sequential addition of water (0.5 mL), 15% NaOH (0.5 mL) and water again(1.5 mL). This was then filtered and solvents evaporated to provide the product as a pale oil (2.75g, 98%). Ri = 0.42 (30% EtOAc/hexanes).
98%
With dimethylsulfide borane complex; In tetrahydrofuran; at 20 - 22℃; for 4.5h;Inert atmosphere;
Borane dimethyl sulfide complex (3.0 mL, 6.1 mmol) was added to a solution of <strong>[42287-90-1]3-(3-bromophenyl)propionic acid</strong> (308 mg, 1.34 mmol) in dry THF (15 mL) at room temperature under inert atmosphere. The mixture was stirred at room temperature for 4.5 h and thereafter diluted with CH2Cl2 and added dropwise to ice-cold 1 M HCl (aq, ~80 mL). NaOH (aq., 10%) was added until pH = 10. The phases were separated and the aqueous phase was extracted with CH2Cl2. The combined organic phases were washed with brine, dried over MgSO4 and concentrated under reduced pressure affording 3-(3-bromophenyl)propanol (282 mg, 98%) as a transparent oil. DMSO (0.28 mL, 3.9 mmol) was added dropwise to a solution of oxalyl chloride (0.14 mL, 1.6 mmol) in dry THF (19 mL) at -78 C under inert atmosphere. The mixture was stirred for 1 h. A solution of the crude alcohol obtained in the previous step (282 mg, 1.31 mmol) in THF (1.5 mL) was added dropwise to the mixture, which was stirred for 1 h at -78 C. Et3N (0.91 mL, 6.6 mmol) was added dropwise and stirring was continued for 20 min at -78 C. Thereafter the mixture was allowed to reach room temperature. Water and EtOAc were added and the phases were separated. The aqueous phase was extracted with EtOAc. The combined organic phases were washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography (10% EtOAc in pentane) affording 17c (209 mg, 73% over two steps) as transparent oil. 1H NMR (400 MHz, CDCl3) delta 9.82 (t, J = 1.2 Hz, 1H), 7.36-7.32 (m, 2H), 7.19-7.10 (m, 2H), 2.97-2.89 (m, 2H), 2.82-2.75 (m, 2H). 13C NMR (100 MHz, CDCl3) delta 200.9, 142.8, 131.5, 130.3, 129.6, 127.2, 122.8, 45.1, 27.8.
28%
With borane-THF; In tetrahydrofuran; at 0 - 20℃;Inert atmosphere;
Into a 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of <strong>[42287-90-1]3-(3-bromophenyl)propanoic acid</strong> (5 g, 21.83 mmol, 1.00 equiv) in THF (50 mL). This was followed by the addition of borane tetrahydrofuran complex solution (1 moL/L, 75 mL, 74.22 mmoL, 3.40 equiv) dropwise with stirring at 0 C. The resulting solution was stirred overnight at room temperature. The reaction mixture was poured into 150 mL of HCl (1 moL/L), extracted with 3×200 mL of DCM, washed with 300 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with DCM/MeOH (10:1). The collected fraction was concentrated to afford 3-(3-bromophenyl)propan-1-ol (1.3 g, 28%) as colorless oil. 1H-NMR (DMSO, 400 MHz) delta(ppm): 7.41-7.20 (m, 4H), 4.51-4.48 (t, 1H), 3.41-3.34 (m, 2H), 2.67-2.59 (m, 2H), 1.73-1.66 (m, 2H).
A suspension of 1.84 g (8 mmol) of <strong>[42287-90-1]3-(3-bromophenyl)propionic acid</strong> and 0.91 g (24 mmol) of sodium borohydride in 20 ml of THF, cooled to 0 C., is admixed in small portions with 3.2 ml (25 mmol) of trifluoroborane-diethyl ether complex. Stirring is continued in the cold for 1 hour, and then at ambient temperature for 16 hours. The reaction mixture is cooled to 0 C. and neutralized to a pH of 7~8 by adding a 1N solution of aqueous sodium hydroxide. It is concentrated under reduced pressure and then the residue is taken up in water. It is extracted with dichloromethane and dried over sodium sulphate. Following filtration, the organic phase is concentrated under reduced pressure. This gives 1.62 g (7.53 mmol) of product in the form of an oil, which is used as it is in the following step.
9.8 g
With borane-THF; In tetrahydrofuran; at 0℃; for 17h;Inert atmosphere; Reflux;
To a cooied (ice bath) soiution of 3-(3-bromophenyi)propanoic acid (8.0 g,35 mmoi) in anhydrous THF (100 mL) was added BH3-THF (100 mL, 1.0 M) via addition funnei under a nitrogen atmosphere. The reaction was stirred at 0 C for 1 h then at refiux for 16 h. The reaction was carefuiiy quenched with HCi (37 mL, 2 M) then concentrated to remove THF. The suspension was diiuted withDCM (300 mL) then fiitered to remove the soiids. The iayers were separatedand the organic phase was washed with water (50 mL) and brine (50 mL) then dried over anhydrous Na2SO4, filtered, and concentrated to give 3-(3-bromophenyl)propan-1-ol (9.8 g, >100%) as a yellow oil, which was used for next step without further purification.
With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20℃; for 18h;
General procedure: To a stirred solution of 3- or 4-substituted phenylpropanoic acid 51-63 (7.0 mmol) in dry THF (35 ml), borane dimethyl sulfide (21.0 mmol) was added dropwise at 0 oC. The reaction mixture was stirred for 18h at room temperature, quenched with H2O and concentrated in vacuo. The resulting residue was re-dissolved in diethyl ether (25 ml), and washed with 10%NaOH (30ml) and brine. The organic fraction was dried over Na2SO4, filtered, and concentrated in vacuo to give 3-phenylpropan-1-ol derivatives that were used in the next step without further purification.
3'-(2-carboxyethyl)-N-[3-[1-(1-methylethyl)-4-piperidinyl]-4-methoxyphenyl]-1,1'-biphenyl-4-carboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In DMF (N,N-dimethyl-formamide); water; at 80℃; for 16h;
A mixture of a solution of the compound of Preparation 6 in dimethylformamide (0.188M, 0.8 [ML,] 0.15 mmol), a solution of 3- bromobenzenepropanoic acid in dimethylformamide [(1M,] 0.3 mL. 0.3 mmol), a solution of [[1,] l'-bis (diphenylphosphino) ferrocene] dichloropalladium [(II)] in dimethylformamide (0.0245M, 0.2 mL), and aqueous 2M sodium carbonate (0.3 mL, 0.6 mmol) was heated to [80C] for 16 h, [CONCENTRATED IN VACUO,] and the residue was purified by HPLC (YMC CombiPrep ODS-A, 50 x 20 mm, 20 [ML/MIN,] A: 0. [1%] trifluoroacetic acid in acetonitrile B: 0.1% aqueous trifluoroacetic acid, A: 10 to 90% during, 10 min, UV detection at 254 nm) to give the title compound. MS (ES) [M/E] 501.2 [[M+H] +]
Stage C: 3-(3-bromophenyl)-propionic acid 18.85 g of product obtained above in 75 ml of water is taken to reflux for 18 hours. Extraction is carried out with isopropyl ether, the extracts are dried, brought to dryness under reduced pressure, and 15.75 g of expected product is obtained. M.p.=74 C.
38
[ 3408-21-7 ]
[ 42287-90-1 ]
benzoic acid N'-[3-(3-bromo-phenyl)-propionyl]-N'-isopropyl-hydrazide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
67%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 18h;
A solution of (<strong>[42287-90-1]3-(3-bromophenyl)propionic acid</strong> (257 mg, 1.12 mmoles) and benzoic acid N'-isopropyl-hydrazide (200 mg, 1.12 mmoles) in DMF (6 mL) was treated with triethylamine (0.47 mL, 3.36 mmoles), HOBT (182 mg, 1.34 mmoles) and EDCI (2.58 mg, 1.34 mmoles) at room temperature for 18 h. The reaction mixture was partitioned between water and dichloromethane. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 20-40% ethyl acetate/hexanes gradient to afford the product as a solid (293 mg, 67%).
To a solution of <strong>[42287-90-1]3-(3-bromophenyl)propionic acid</strong> (93) (5.0 g, 21.8 mmol) and iV- hydroxysuccinimide (2.51 gr., 21.8 mmole) in CH2CI2 (100 ml) was added dicyclohexylcarbodiimide (4.50 g, 21.8 mmol) and the mixture was stirred at room temperature for 45 min. The precipitate was removed by filtration and the filtrate was cooled in an ice bath. Ammonia gas was bubbled into the solution for 2 min then allowed to warm to room temperature overnight. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in EtOAc. This solution was washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated under reduced pressure to an oil which was triturated with hexanes. The product was collected by filtration to give 3-(3-bromophenyl)propionamide (94) as a white solid.This material was taken on to the next synthetic step without further purification. Yield (4.62 g, 93%): 1H NMR (400 MHz, DMSO-d6) delta 7.40 (s, 1H), 7.35 (dt, J = 6.4, 2.4 Hz, 1H), 7.26 (br s, 1H), 7.18-7.24 (m, 2H), 6.75 (br s, 1H), 2.78 (t, J = 7.6 Hz, 2H), 2.34 (t, J= 7.6 Hz, 2H).
Ethyl 3-(3-bromophenyl)propanoate (Scheme 1, A). To a solution of 3-(3-bromophenyl)-propionic acid(25.0 g, 109 mmol) in DCM (300.0 mL) was added oxalyl chloride (11.9 mL, 136 mmol) and 2 drops of DMF. After stirring for 2 h the solution was concentrated under reduced pressure, dissolved in DCM (80 mL), and cooled to -10 C. To this solution, ethanol (80 mL) was added dropwise and stirred at room temperature for 4 h. The solution was concentrated under reduced pressure and dried under vacuum to afford the product in quantitative yield. 1H NMR (300 MHz, DMSO) delta 7.45 (s, IH), 7.38 (mult IH), 7.24 (d, J= 20.8 Hz, 2H), 4.04 (q, J= 7.1 Hz, 2H), 2.84 (t, J= 7.5 Hz, 2H), 2.62 (t, J= 7.5 Hz, 2H), 1.15 (t,J= 7.1 Hz, 3H); m/z 258.
92%
With sulfuric acid; at 90℃; for 5h;
PREPARATION 30 Ethyl 3-(3-bromophenyl)propanoate 2 g (8.38 mmols) of <strong>[42287-90-1]3-(3-bromophenyl)propanoic acid</strong> was dissolved in 25 mL ethanol. 2.10 mL sulphuric acid (39.4 mmols) was added and the mixture was heated at 90C for 5 hours. The mixture was allowed to cool and was evaporated. The residue was taken up in water and basified to pH 9 with NaOH 32%. The aqueous was then extracted five times with dichloromethane. The organic phase was dried over magnesium sulphate. Purification by chromatography (hexane 100% to ethyl acetate 100%) gave 2.04g (92%) of the title compound. HPLC/MS (10 min) retention time 6.81 min LRMS: m/z 257 (M+)
With hydrazine hydrate;bis(triphenylphosphine)palladium(II)-chloride; In tetrahydrofuran; water; ethyl acetate;
4.1. 3-(3'-Benzyloxybiphenyl-3-yl)propionic acid 21.5 g (77.2 mmol) of sodium metaborate octahydrate, 0.700 g (977 mmol) of bis(triphenylphosphine)palladium(II) chloride, 0.1 ml (2 mmol) of hydrazine hydrate and 10.0 g (42.3 mmol) of <strong>[42287-90-1]3-(3-bromophenyl)propionic acid</strong> are initially introduced in 10 ml of tetrahydrofuran and 30 ml of water, and a solution of 10.0 g (43.9 mmol) of 3-benzyloxy-benzeneboronic acid in 30 ml of THF is added. The batch is subsequently heated under reflux overnight, added to water and extracted three times with MTB ether. The combined org. phases are filtered through silica gel with heptane/ethyl acetate (1:1), and the crude product is recrystallised from toluene, giving 3-(3'-benzyloxybiphenyl-3-yl)propionic acid as a colourless solid.
Example 37A: methyl 3-(3-bromophenyl)propanoate j00412j <strong>[42287-90-1]3-(3-bromophenyl)propanoic acid</strong> (1 g, 4.37 mmol) was dissolved in MeOH(17.46 mL). SOC12 (1.593 mL, 21.83 mmol) was added dropwise, and the reactionheated to reflux for 3 h. The reaction was concentrated in vacuo to yield Example 37A (1.08 g, 100%). 1H NMR (400 MHz, CHLOROFORM-d) oe ppm 7.30 - 7.42 (2 H, m), 7.06 - 7.21 (2 H, m), 3.67 (3 H, s), 2.92 (2 H, t, J=7.78 Hz), 2.62 (2 H, t, J=7.65 Hz).
99%
With sulfuric acid; for 16.0h;Reflux;
General procedure: In distinct reactors, solutions of the appropriate 3-(3-bromophenyl)-propionic acid or 3-(4-Bromophenyl)-propionic acid in MeOH were prepared and concentrated H2SO4 was added to each reactor. The resulting mixtures were stirred under reflux for 16h. Each crude mixture was reduced under vacuo and the residues were partitioned with dichloromethane (20 mL) and saturated NaHCO3 solution (20 mL). The organic layers of each reaction was dried with Na2SO4, filtered and evaporated. The resulting compounds were used in a further reaction without any further purification.
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