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[ CAS No. 53087-13-1 ]

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Chemical Structure| 53087-13-1
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CAS No. :53087-13-1 MDL No. :MFCD00155065
Formula : C13H11BrO Boiling Point : 333.5°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :263.13 g/mol Pubchem ID :2756638
Synonyms :

Safety of [ 53087-13-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P273-P301+P312-P330 UN#:N/A
Hazard Statements:H302-H413 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 53087-13-1 ]

  • Upstream synthesis route of [ 53087-13-1 ]
  • Downstream synthetic route of [ 53087-13-1 ]

[ 53087-13-1 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 591-20-8 ]
  • [ 100-44-7 ]
  • [ 53087-13-1 ]
YieldReaction ConditionsOperation in experiment
93% With potassium carbonate In ethanol for 4 h; Reflux To a suspension of m-bromophenol (1) (15.57 g, 90 mmol) in dehydrated alcohol (300 mL) was added anhydrous potassium carbonate (37.32 g, 270 mmol) and benzyl chloride (11.50 mL, 99 mmol). The mixture was refluxed for 4 h. Filtration and evaporation of alcohol was done in a vacuum. The residue was extracted with EtOAc. The combined organic layers were washed with water, NaOH (2 M), brine, and HCl (2 M), dried over Na2SO4, and concentrated to give (2) (22.02 g, 93percent) as a yellow solid. A 250 mL, two-necked, round-bottomed flask containing dry magnesium (2.18 g, 90 mmol) and iodine (trace) was equipped with two rubber septum stirred under the protection of nitrogen. The solution of (2) (15.79 g, 60 mmol) in 40 mL of anhydrous THF was added slowly into the flask through a syringe at a rate to remain reflux. After addition finishing, the resulting mixture was kept in refluxing for 5 h with stirring. The mixture in cooled to -30 °C, then the trimethylborate (9.36 g, 90 mmol) in 60 mL of anhydrous THF was added slowly through a syringe. After addition finishing, the resulting mixture was allowed to stir at room temperature for overnight and then treated with saturated NH4Cl solution, stirred for 1 h at room temperature. Then THF was removed by rotary evaporation. The aqueous layer was extracted with EtOAc and dried over Na2SO4, filtered and concentrated to afford the yellow crude product. The crude product was purified by recrystallization from water affording (3) as a white solid (7.53 g, 55percent).
1.6 g With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 2 h; (1) 0.77 g of benzyl chloride was dropwise added to a mixed solution comprising 1.0 g of 3-bromophenol, 1.6 g of potassium carbonate and 5 mL of N,N- dimethylformamide. After completion of the dropwise addition, a reaction was carried out at 60°C for 2 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. Then, the organic layer was washed with water and an aqueous sodium chloride solution, and anhydrous sodium sulfate was added for drying. The solvent was distilled off under reduced pressure to obtain 1.6 g of oily 1 - (benzyloxy)-3-brornobenzene.
Reference: [1] Journal of Materials Chemistry, 2010, vol. 20, # 15, p. 3069 - 3078
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 5, p. 1044 - 1054
[3] Journal of Medicinal and Pharmaceutical Chemistry, 1962, vol. 5, p. 752 - 762
[4] Patent: US5447656, 1995, A,
[5] Patent: EP838461, 1998, A2,
[6] Patent: US2007/209123, 2007, A1, . Location in patent: Page/Page column 8
[7] Patent: WO2013/27660, 2013, A1, . Location in patent: Page/Page column 21
[8] Macromolecules, 2016, vol. 49, # 10, p. 3706 - 3715
[9] Patent: CN104016879, 2016, B, . Location in patent: Paragraph 0045; 0046
[10] Patent: CN103980153, 2016, B, . Location in patent: Paragraph 0048; 0049; 0050
  • 2
  • [ 591-20-8 ]
  • [ 100-39-0 ]
  • [ 53087-13-1 ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate In acetone for 15 h; Reflux A solution of 3-bromophenol (3 g, 17.34 mmol) in acetone (100 mL) was added with benzyl bromide (2.2 mL, 19.07 mmol) and K2CO3 (7.0 g, 52.02 mmol), and the resulting mixture was refluxed for 15 hours. The reaction mixture was cooled to room temperature, filtered, and washed with acetone. The filtrate was concentrated and purified by silica gel chromatography to obtain the title compound (white solid, 5.1 g, 100percent yield). 1H NMR (300 MHz, CDCl3) δ 7.50 - 7.30 (m, 5H), 7.20 - 7.01 (m, 3H), 6.98 - 6.80 (m, 1H), 5.05 (s, 2H).
96% With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 20 h; Example 81 3- {2-Methyl-4- [3- (2-phenoxy-4-trifluoromethyl-phenoxy)-phenoxy]-phenyl}-propionic acid Step A 3-Benzyloxy-1-bromobenzene A mixture of 3-bromophenol (10. 0 g, 57.8 mmol) and 325 mesh potassium carbonate (8.79 g, 63.6 mmol) in DMF (100 mL) is treated dropwise with benzyl bromide (9.89 g, 57.8 mmol) and then stirred 20 hours at rt under N2. The reaction is filtered, and the filtrate is acidified with 1 N HCI. The mixture is then diluted with water and extracted with Et20. The organic layer is dried (Na2S04), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 10/1 hexanes/ethyl acetate to afford 14.55 g (96percent) of the titled compound. Rf= 0.86 (4/1 hexanes/EtOAc). IH NMR (400 MHz, CDC13).
79% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12 h; Step-1: Synthesis of l-(benzyloxy)-3-bromobenzene BnBr/K2C03 DMF HO Br RT/12 h BnO Br To a solution of 3-bromophenol (5 g, 28.9 mmol)' in DMF (50 mL), were added potassium carbonate (11.9 g, 86.7 mmol) and benzyl bromide (5.9 g, 34.6 mmol) sequentially at room temperature. The resulting mixture was stirred at room temperature for 12 h, completion of the reaction was monitored by TLC. The reaction mixture was cooled to room temperature, diluted with water, extracted with ethyl acetate. The organic layer was dried over anhydrous Na2S04i concentrated under reduced pressure. The crude compound was purified over 230- 400 mesh silica gel column chromatography using 8percent EtOAc in n-hexane to afford 1- (benzyloxy)-3-bromobenzene (6 g, 79percent).
67% With potassium carbonate In hexane; dichloromethane; water; acetone 4.6.2.19 3-(3-Benzyloxy-phenyl)-3-(3,5-dimethoxy-phenyl)-acrylonitrile
To a stirred solution of bromomethylbenzene (24.39 g, 143 mmol), 3-bromophenol (24.92 g, 144 mmol) in acetone (20 ml) was added potassium carbonate (59.72 g, 430 mmol).
The suspension was refluxed overnight and then evaporated.
To the residue was added H2O (100 ml) and extracted with EtOAc (3*80 ml).
The combined EtOAc extracts were back washed with Na2CO3 and then dried over MgSO4, filtered and evaporated to get an off-white solid, which was purified via flash column chromatography (10percent CH2Cl2 in hexane) to give 1-benzyloxy-3-bromo-benzene as a white solid (10 g, 67percent): 1H-NMR (DMSO-d6) 7.46-7.00 (m, 9H, Ar), 5.12 (s, 2H, CH2).
The product was carried over to the next step.
67% With potassium carbonate In water; acetone 4.6.2.95 (E/Z)-3-(3,5-Dimethoxy-phenyl)-3-(3-ethoxy-phenyl)-acrylonitrile
To a stirred solution of benzyl bromide (24.39 g, 142.6 mmol) and 3-bromo phenol (24.92 g, 144 mmol) in 20 mL of fresh acetone was added potassium carbonate (59.72 g, 432 mmol).
The suspension was refluxed overnight.
The mixture was evaporated and added water (100 mL), extracted with EtOAc (3*80 mL).
The combined EtOAc extracts were back washed with water (100 mL), dried over MgSO4, filtered and evaporated to give 1-benzyloxy-3-bromo-benzene as an off-white solid (10.0 g, 67percent yield): 1H NMR (DMSO-d6) δ 5.12 (s, 2H, CH2), 7.00-7.46 (m, 9H, Ar).
67% With potassium carbonate In water; acetone 4.6.2.96 Z-3-(3,5-Dimethoxy-phenyl)-3-(3-hydroxy-phenyl)-acrylonitrile
To a stirred solution of benzyl bromide (24.39 g, 142.6 mmol) and 3-bromo phenol (24.92 g, 144 mmol) in 20 mL of fresh acetone was added potassium carbonate (59.72 g, 432 mmol).
The suspension was refluxed overnight.
The mixture was evaporated and added water (100 mL), extracted with EtOAc (3*80 mL).
The combined EtOAc extracts were back washed with water (100 mL), dried over MgSO4, filtered and evaporated to give 1-benzyloxy-3-bromo-benzene as an off-white solid (10.0 g, 67percent yield): 1H NMR (DMSO-d6) δ 5.12 (s, 2H, CH2), 7.00-7.46 (m, 9H, Ar).
59% With potassium carbonate In acetone for 3 h; Heating / reflux REFERENCE EXAMPLE 1
3-(Benzyloxy)bromobenzene
3-Bromophenol (50 g, 0.289 mol) was dissolved in acetone (500 ml), anhydrous potassium carbonate (80 g, 0.580 mmol) and benzyl bromide (59 g, 0.345 mol) were successively added thereto and the mixture was heated to reflux for 3 hours.
The reaction mixture was filtered and the filtrate was concentrated under reduced pressure.
The resulting crude reaction product was recrystallized (hexane was used as a solvent and the recrystallization operation was carried out twice) to give the title compound (45.0 g, 0.171 mol, 59percent).
57% With potassium carbonate In acetone for 4 h; Reflux Intermediate 21 : 1-(benzyloxy)-3-bromobenzene A mixture of 3-bromophenol (2.60 g, 1.59 mL, 15 mmol), benzyl bromide (2.82 g 1.96 mL, 16.5 mmol) and potassium carbonate (2.07 g, 15 mmol) in acetone (25 mL) was refluxed for 4 hours. The reaction mixture was cooled to room temperature. The mixture was filtered and the solvent was evaporated from the filtrate. The residue was purified by chromatography on silica gel eluting with 0- 25 percent ethyl acetate/hexane. Appropriate fractions were combined and evaporated. The impure product was re-purified by chromatography on silica gel eluting with 0-10 percent ethyl acetate/hexane to give 1-(benzyloxy)-3-bromobenzene (2.25 g, 8.55 mmol, 57.0 percent yield) as a white solid. 1H NMR (400MHz, DMSO-d6) δ-ppm 7.46-7.32 (m, 5H), 7.27-7.22 (m, 2H), 7.13 (m,1 H), 7.03 (m,
26 g With potassium carbonate In acetone for 2 h; Reflux To a mixture of 3-bromophenol (20 g, 0.115 mol) and potassium carbonate (95 g, 0.69 mol, 6 eq) in acetone (500 ml) was added benzyl bromide (15.12 ml, 0.127 mol, 1.1 eq). The reaction mixture was heated at reflux for 2 hours (TLC showed completion of reaction). The reaction mixture was filtered, washed with acetone and the filtrate was evaporated to dryness. The residue was dissolved in water (200 ml) and ethyl acetate (200 ml). The layers were separated. The organic layer was washed with brine (200 ml), dried over sodium sulfate, filtered and evaporated to dryness. The crude was recrystallized from hexane to give the title compound (26 g) 3 as a white solid. MP 61-62° C.

Reference: [1] Journal of Organic Chemistry, 2005, vol. 70, # 18, p. 7087 - 7092
[2] Patent: EP2963027, 2016, A1, . Location in patent: Paragraph 1227; 1228; 1229
[3] Patent: WO2005/37763, 2005, A1, . Location in patent: Page/Page column 123-124; 138
[4] Synthetic Communications, 2009, vol. 39, # 18, p. 3243 - 3253
[5] MedChemComm, 2017, vol. 8, # 2, p. 471 - 478
[6] Patent: WO2016/196342, 2016, A1, . Location in patent: Page/Page column 140; 141
[7] Synthesis (Germany), 2017, vol. 49, # 2, p. 275 - 292
[8] Tetrahedron, 2005, vol. 61, # 41, p. 9688 - 9695
[9] Patent: US2005/107339, 2005, A1,
[10] Patent: US2005/107339, 2005, A1,
[11] Patent: US2005/107339, 2005, A1,
[12] Patent: US2004/39061, 2004, A1, . Location in patent: Page/Page column 9
[13] Patent: WO2014/140077, 2014, A1, . Location in patent: Page/Page column 44
[14] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 13, p. 3477 - 3480
[15] Patent: US6441017, 2002, B1,
[16] Patent: US5521192, 1996, A,
[17] Patent: EP1314712, 2003, A1,
[18] Patent: WO2007/120595, 2007, A2, . Location in patent: Page/Page column 93
[19] Journal of Medicinal Chemistry, 2012, vol. 55, # 12, p. 5760 - 5773
[20] Patent: WO2017/40449, 2017, A1, . Location in patent: Paragraph 00245
[21] Patent: US2017/176476, 2017, A1, . Location in patent: Paragraph 0009; 0079
  • 3
  • [ 585-79-5 ]
  • [ 100-51-6 ]
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Reference: [1] Chemische Berichte, 1991, vol. 124, # 1, p. 163 - 173
  • 4
  • [ 591-20-8 ]
  • [ 100-39-0 ]
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Reference: [1] Patent: US5098930, 1992, A,
  • 5
  • [ 591-20-8 ]
  • [ 584-08-7 ]
  • [ 100-44-7 ]
  • [ 53087-13-1 ]
Reference: [1] Patent: US5952350, 1999, A,
[2] Patent: US5843940, 1998, A,
  • 6
  • [ 591-20-8 ]
  • [ 100-44-7 ]
  • [ 53087-13-1 ]
Reference: [1] Patent: EP838459, 1998, A1,
  • 7
  • [ 53087-13-1 ]
  • [ 34068-01-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 13, p. 3477 - 3480
  • 8
  • [ 53087-13-1 ]
  • [ 1484-26-0 ]
Reference: [1] Nature Chemistry, 2017, vol. 9, # 7, p. 681 - 688
[2] Journal of the American Chemical Society, 2007, vol. 129, # 34, p. 10354 - 10355
  • 9
  • [ 53087-13-1 ]
  • [ 5419-55-6 ]
  • [ 156682-54-1 ]
Reference: [1] Patent: US5977105, 1999, A,
[2] Patent: US5843940, 1998, A,
[3] Patent: EP838461, 1998, A2,
[4] Patent: EP1080070, 2006, B1, . Location in patent: Page/Page column 13
  • 10
  • [ 53087-13-1 ]
  • [ 121-43-7 ]
  • [ 156682-54-1 ]
Reference: [1] Patent: US5447656, 1995, A,
[2] Patent: CN104016879, 2016, B, . Location in patent: Paragraph 0047; 0048; 0049
[3] Patent: CN103980153, 2016, B, . Location in patent: Paragraph 0048; 0051; 0052; 0053
  • 11
  • [ 53087-13-1 ]
  • [ 156682-54-1 ]
Reference: [1] Journal of Materials Chemistry, 2010, vol. 20, # 15, p. 3069 - 3078
[2] Synthetic Communications, 2007, vol. 37, # 1, p. 129 - 135
[3] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 5, p. 1044 - 1054
  • 12
  • [ 53087-13-1 ]
  • [ 688-71-1 ]
  • [ 156682-54-1 ]
Reference: [1] Patent: US5952350, 1999, A,
[2] Patent: EP838459, 1998, A1,
  • 13
  • [ 53087-13-1 ]
  • [ 73183-34-3 ]
  • [ 765908-38-1 ]
Reference: [1] Patent: US2007/209123, 2007, A1, . Location in patent: Page/Page column 8
[2] Patent: WO2014/140077, 2014, A1, . Location in patent: Page/Page column 44
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