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[ CAS No. 105-13-5 ]

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Chemical Structure| 105-13-5
Chemical Structure| 105-13-5
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CAS No. :105-13-5 MDL No. :MFCD00004653
Formula : C8H10O2 Boiling Point : 259°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :138.16 g/mol Pubchem ID :7738
Synonyms :

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Signal Word:Warning Class:N/A
Precautionary Statements:P501-P270-P264-P280-P337+P313-P305+P351+P338-P302+P352-P332+P313-P362-P301+P312+P330 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
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Application In Synthesis of [ 105-13-5 ]

  • Upstream synthesis route of [ 105-13-5 ]
  • Downstream synthetic route of [ 105-13-5 ]

[ 105-13-5 ] Synthesis Path-Upstream   1~37

  • 1
  • [ 329060-91-5 ]
  • [ 494-19-9 ]
  • [ 105-13-5 ]
Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 48, p. 15267 - 15271
  • 2
  • [ 105-13-5 ]
  • [ 2746-25-0 ]
YieldReaction ConditionsOperation in experiment
94% With phosphorus tribromide In dichloromethane at 0 - 20℃; Example 10
Preparation of 4-methoxybenzylic Bromide (13)
Phosphorus tribromide (6.2 g; 25.0 mmol; 1.15 eq.) is added to a 4-methoxybenzylic alcohol solution (3 g; 21.7 mmol; 1 eq.), cooled to 0° C., in dichloromethane (35 ml).
After 5 h at room temperature, the reaction mixture is poured into ice water (100 ml) and then is extracted with ether (3*100 ml).
The organic phase is washed, dried on MgSO4, filtered and evaporated to obtain 4.1 g of a colorless oil.
Yield: 94percent
Empirical formula: C8H9BrO
90% With phosphorus pentoxide; potassium bromide In acetonitrile at 20℃; for 0.416667 h; General procedure: To a mixture of alcohol (1 mmol) and KBr (1.5 mmol, 0.18 g) in acetonitrile (5 mL), P2O5 (1.5 mmol, 0.23 g) was added and the reaction was stirred at room temperature for the time specified in Table 3. After reaction completion (TLC or GC), the reaction mixture was filtered and the residue washed with ethyl acetate (3 × 8 mL). The combined organic layers were washed with water (10 mL) and dried over Na2SO4. The solvent was removed under reduced pressure to afford the corresponding product. If necessary, further purification was performed by column chromatography.
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  • [ 104-21-2 ]
  • [ 2746-25-0 ]
YieldReaction ConditionsOperation in experiment
86% With N-Bromosuccinimide; triphenylphosphine In acetonitrile at 20℃; for 1.9 h; Cooling with ice General procedure: To a solution of Ph3P(OAc)2, was added 3-phenylpropanol (1 mmol, 0.137 mL). The progress of the reaction was monitored by TLC (Table 3, entry 2). After completion of the reaction (0.3 h) the reaction mixture was filtered to remove the precipitated NH4Br followed by evaporation of the solvent. Column chromatography of the crude mixture on silica gel using n-hexane/EtOAc (3:1) as the eluent gave 3-phenylpropyl acetate in 90percent yield (0.159 g).
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 14, p. 1813 - 1816
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  • [ 824-94-2 ]
YieldReaction ConditionsOperation in experiment
86 %Spectr. With 1-pyrrolidinecarboxaldehyde; benzoyl chloride; sodium bromide In acetone at 0 - 20℃; for 20.5 h; General procedure: Using 10 molpercent of FPyr benzyl bromide 85 was prepared with BzCI (1.2 equiv) according to general procedure VIII (chapter 4.9.1, t = 20 h, T = rt) in 86percent yield (internal standard). Moreover, 4- methoxybenzyl chloride 25 was obtained in 14percent yield (ratio bromide 85/chloride 25 86:14) togetherwith 4-methoxybenzyl benzoate 35 in 2percent yield (ratio 85+25/35 97:3).
Reference: [1] Patent: WO2016/202894, 2016, A1, . Location in patent: Page/Page column 182; 183; 184
  • 5
  • [ 105-13-5 ]
  • [ 2746-25-0 ]
  • [ 123-11-5 ]
Reference: [1] Journal of Organic Chemistry, 1999, vol. 64, # 4, p. 1191 - 1196
  • 6
  • [ 60-29-7 ]
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Reference: [1] Patent: US5229381, 1993, A,
  • 7
  • [ 558-13-4 ]
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Reference: [1] Patent: US5753679, 1998, A,
  • 8
  • [ 123-72-8 ]
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  • [ 6963-56-0 ]
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  • 9
  • [ 67-66-3 ]
  • [ 7726-95-6 ]
  • [ 105-13-5 ]
  • [ 50-00-0 ]
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  • [ 2746-25-0 ]
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  • 10
  • [ 10035-10-6 ]
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  • [ 2746-25-0 ]
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[2] Monatshefte fuer Chemie, 1913, vol. 34, p. 1998
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  • [ 5440-80-2 ]
  • [ 123-11-5 ]
  • [ 104-27-8 ]
Reference: [1] Catalysis Science and Technology, 2017, vol. 7, # 9, p. 1928 - 1936
  • 12
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  • [ 34841-06-0 ]
YieldReaction ConditionsOperation in experiment
55 %Chromat. With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In dichloromethane at 25℃; for 0.5 h; General procedure: DBDMH (1 mmol) was added to a mixture of 1b (1 mmol) and dichloromethane (20ml). The reaction was kept at room temperature. After the mixture was stirred for0.5h, the mixture was washed with water (330 ml),dried with anhydrous MgSO4,filtered, and vacuum evaporated. The residue was purified by column chromatography (silica gel: petroleum ether/ethyl acetate, 30:1) to afford the product as light yellowsolid (93percent yield).
Reference: [1] Synthetic Communications, 2014, vol. 44, # 8, p. 1155 - 1164
  • 13
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  • [ 123-11-5 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 21, p. 3681 - 3684
  • 14
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  • [ 37116-80-6 ]
Reference: [1] Tetrahedron, 1976, vol. 32, p. 109 - 113
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Reference: [1] Bulletin of the Chemical Society of Japan, 1965, vol. 38, p. 1032 - 1034
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  • [ 2314-37-6 ]
  • [ 123-11-5 ]
YieldReaction ConditionsOperation in experiment
71% With iodic acid In N,N-dimethyl-formamide at 60℃; for 2 h; Inert atmosphere General procedure: To a solution of p-bromobenzyl alcohol I-1 (187 mg, 1.0 mmol) in DMF (2.0 mL) was added HIO3 (194 mg, 1.1 mmol). The mixture was stirred at 60 °C for 2 h under an Ar atmosphere. After the reaction, the reaction mixture was poured into aq Na2S2O3, and extracted with a mixture of Et2O: hexane=1:1 (3*10 mL). The organic layer was dried over Na2SO4. After being filtration and removal of the solvent under reduced pressure, the residue was purified by flash short column chromatography on silica gel (EtOAc-hexane, 1:4) to give p-bromobenzaldehyde II-1 in 95percent yield.
71% With iodic acid In N,N-dimethyl-formamide at 20 - 60℃; for 2 h; Inert atmosphere General procedure: 4-Bromobenzyl alcohol (187 mg, 1.0 mmol)Was dissolved in 2.0 mL of DMF solvent,This was mixed with iodic acid (194 mg, 1.1 mmol).The mixture was stirred for 2 hours at room temperature to 60 ° C. in an Ar atmosphere.To the reaction mixture was added aqueous sodium thiosulfate solution and extracted with diethyl ether: hexane = 1: 1 (3 × 10 mL).The extract was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.The residue was purified by silica gel column chromatography (ethyl acetate: hexane = 1: 4) to give 4-bromobenzaldehyde as a final product (yield 91percent). The same treatment was carried out except that the primary alcohol or secondary alcohol was used instead of 4-bromobenzyl alcohol used in Example 1 based on the following general formula (1) to obtain a carbonyl compound shown in Table 1 Were obtained in yields shown in Table 1, respectively.
Reference: [1] Tetrahedron, 2016, vol. 72, # 44, p. 6948 - 6954
[2] Patent: JP2018/2680, 2018, A, . Location in patent: Paragraph 0032-0035
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  • [ 121-98-2 ]
  • [ 67-63-0 ]
  • [ 18228-46-1 ]
  • [ 261930-06-7 ]
  • [ 105-13-5 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 3, p. 862 - 867
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  • [ 105-13-5 ]
  • [ 13807-89-1 ]
YieldReaction ConditionsOperation in experiment
78% With Amberlyst-15 In dichloromethane for 3.5 h; Reflux General procedure for selective mono PMB protection of diols: (Z)-4-((4-Methoxybenzyl)oxy)but-2-en-1-ol (Table 5, entry 1): A mixture of cis-2-butene-1,4-diol (200 mg, 2.3 mmol), p-anisyl alcohol (345 mg, 2.5 mmol), and catalytic amount (10percent w/w, 20 mg) of Amberlyst-15 resin in anhydrous CH2Cl2 (10 mL) was refluxed. After 3 h, the crude reaction mixture was filtered through a Whatman filter paper and the residue washed with CH2Cl2, dried (over anhydrous Na2SO4), filtered and concentrated in vacuo and purified using flash chromatography (pet ether/ethyl acetate 70:30) to provide 401 mg (85percent) of pure product as a colorless dense liquid.
78% With Amberlyst-15 resin In dichloromethane for 3.5 h; Reflux A mixture of ethylene glycol (0.31 g, 5 mmol), 4-methoxybenzyl alcohol (0.75g, 5.43 mmol), and catalytic amount of Amberlyst-15 resin (31 mg, 10percent w/w) in anhydrous dichloromethane (20 mL) was refluxed for 3.5 h. The crude reaction mixture was filtered through a Whatman filter paper and the residue washed with dichloromethane (50 mL), dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel using 40-50percent EtOAc/hexane (v/v) as the eluent to afford a compound III (0.71 g, 3.9 mmol) in 78percent yield as a colourless liquid. TLC: Rf 0.2 (40percent EtOAc/hexane). IR (neat): 3422, 2934, 2863, 1611, 1513, 1461, 1248, 1106, 1033, 820 cm-1; 1H NMR (500 MHz, CDCl3): δ 7.27 (d, J = 8.7 Hz, 2H), 6.89 (d, J = 8.7 Hz, 2H), 4.49 (s, 2H), 3.80 (s, 3H), 3.74 (t, J = 4.4 Hz, 2H), 3.57 (td, J = 4.4, 1.8 Hz, 2H), 2.15-2.07 (bs, 1H); 13C NMR (125 MHz, CDCl3): δ 158.7, 129.6, 128.9, 113.2, 72.2, 70.8, 60.9, 54.6; MS (ESI): m/z 205 [M+Na]+. HRMS (ESI): calcd for C10H14O3Na: 205.0841, found: 205.0840.
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 35, p. 4683 - 4686
[2] Tetrahedron, 2018, vol. 74, # 10, p. 1071 - 1077
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  • [ 105-13-5 ]
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YieldReaction ConditionsOperation in experiment
64%
Stage #1: With hydrogenchloride In diethyl ether; water for 3 h;
Stage #2: With sodium hydroxide In diethyl ether; ethanol; water at 20℃; for 2 h;
Stage #3: With hydrogenchloride In diethyl ether; ethanol; water at 0℃;
4-Methoxybenzyl alcohol (280 g, 1780 mmol) dissolved in diethylether (400 mL) was added in drops to a mixture of diethylether (400 niL) and cone, hydrochloric acid (400 mL) over 2 h, and the mixture was stirred for 1 h. The organic layer was separated, and added to a solution prepared by dissolving L-cysteine (197 g, 1625 mmol) and 2N aqueous sodium hydroxide solution (980 mL) to ethanol (1890 mL).The mixture was stirred for 2 h at room temperature. After completion of the reaction, the reaction mixture was cooled to 0°C, and neutralized to pH 7 using 3N aqueous hydrochloric acid solution. The resulting solid was filtered and dried to give the title compound (250 g, Yield 64percent).
64%
Stage #1: With hydrogenchloride In diethyl ether
Stage #2: With sodium hydroxide In diethyl ether; ethanol; water at 20℃; for 2 h;
Stage #3: With hydrogenchloride In diethyl ether; ethanol; water at 0℃;
4-Methoxybenzyl alcohol (280 g, 1780 mmol) dissolved in diethylether (400 mL) was added in drops to a mixture of diethylether (400 mL) and conc. hydrochloric acid (400 mL) over 2 h, and the mixture was stirred for 1 h. The organic layer was separated, and added to a solution prepared by dissolving L-cysteine (197 g, 1625 mmol) and 2N aqueous sodium hydroxide solution (980 mL) to ethanol (1890 mL). The mixture was stirred for 2 h at room temperature. After completion of the reaction, the reaction mixture was cooled to 0°, and neutralized to pH 7 using 3N aqueous hydrochloric acid solution. The resulting solid was filtered and dried to give the title compound (250 g, Yield 64percent).
64%
Stage #1: With hydrogenchloride In diethyl ether; water for 3 h;
Stage #2: With sodium hydroxide In diethyl ether; ethanol; water at 20℃; for 2 h;
Stage #3: With hydrogenchloride In diethyl ether; ethanol; water
To a solvent mixture of diethylether (400 ml) and conc. hydrochloric acid (400 ml) was added in drops 4-methoxybenzylalcohol (280 g, 1780 mmol) dissolved in diethylether (400 ml) for 2 h, and the mixture was stirred for 1 h. The organic layer was separated, and added to a solution prepared by dissolving L-cysteine (197 g, 1625 mmol) and 2N aqueous sodium hydroxide solution (980 ml) in ethanol (1890 ml). The mixture was stirred for 2 h at room temperature. After completion of the reaction, the reaction solution was cooled to 0° C., and neutralized to pH 7 using 3N aqueous hydrochloric acid solution. The resulting solid was filtered, and dried to give (R)-2-amino-3-(4-methoxy-benzylsulfanyl)-propionic acid (250 g, 1035 mmol, Yield: 64percent).
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[3] Patent: US2010/267708, 2010, A1, . Location in patent: Page/Page column 23-24
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  • 27
  • [ 105-13-5 ]
  • [ 3168-59-0 ]
Reference: [1] Journal of Organic Chemistry, 1960, vol. 25, p. 334 - 343
  • 28
  • [ 104-47-2 ]
  • [ 105-13-5 ]
  • [ 72035-46-2 ]
Reference: [1] ACS Catalysis, 2018, vol. 8, # 10, p. 9226 - 9231
  • 29
  • [ 105-13-5 ]
  • [ 78507-19-4 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1911, vol. <4> 9, p. 824
[2] Bulletin de la Societe Chimique de France, 1911, vol. <4> 9, p. 824
  • 30
  • [ 79-08-3 ]
  • [ 105-13-5 ]
  • [ 88920-24-5 ]
YieldReaction ConditionsOperation in experiment
71% With sodium hydride In tetrahydrofuran; mineral oil at 0 - 23℃; for 4 h; To a solution of (4-methoxyphenyl)methanol (1 equiv.) and 2-bromoacetic acid (1.2 equiv.) in anhydrous THF at 0 °C was added sodium hydride (60percent w/w in mineral oil, 3 equiv.) in 3 portions. The mixture was stirred at 70 °C for 4 h. After cooling to ambient temperature, water was added the resultant mixture was washed with hexanes. The aqueous phase was acidified to pH 2 with iN HC1 and extracted with ethyl acetate. The organic layer was dried, filtered and the solvent was removed in vacuo. Purification via silica gel chromatography with 50percent ethyl acetate in hexanes delivered 2-((4-methoxybenzyl)oxy)acetic acid (0.51 g, 71percent yield) as a clear solid.1H NMR (500 MHz, CDC13) ö ppm 7.29 (m, 2 H), 6.90 (m, 2 H), 4.59 (s, 2 H), 4.10 (s, 2 H),3.81 (s, 3 H).
Reference: [1] Bioorganic and medicinal chemistry letters, 2001, vol. 11, # 21, p. 2837 - 2841
[2] Synlett, 2012, vol. 23, # 19, p. 2845 - 2849
[3] Tetrahedron Letters, 2002, vol. 43, # 41, p. 7427 - 7429
[4] Patent: WO2014/144100, 2014, A2, . Location in patent: Paragraph 00274
[5] Patent: WO2006/109729, 2006, A1, . Location in patent: Page/Page column 138-139
[6] Journal of Medicinal Chemistry, 1984, vol. 27, # 8, p. 967 - 978
[7] Journal of Organic Chemistry, 1996, vol. 61, # 13, p. 4369 - 4373
[8] Patent: US5811550, 1998, A,
[9] Journal of Organic Chemistry, 2008, vol. 73, # 11, p. 4338 - 4341
[10] Journal of Organic Chemistry, 2011, vol. 76, # 9, p. 3576 - 3581
[11] Journal of Medicinal Chemistry, 2017, vol. 60, # 12, p. 5162 - 5192
  • 31
  • [ 79-11-8 ]
  • [ 105-13-5 ]
  • [ 88920-24-5 ]
Reference: [1] Chemical Communications, 1997, # 19, p. 1919 - 1920
[2] Tetrahedron Letters, 2008, vol. 49, # 23, p. 3762 - 3765
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, # 10, p. 2479 - 2483
  • 32
  • [ 105-36-2 ]
  • [ 105-13-5 ]
  • [ 88920-24-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 1998, vol. 6, # 11, p. 2061 - 2073
  • 33
  • [ 616-45-5 ]
  • [ 105-13-5 ]
  • [ 72432-10-1 ]
Reference: [1] Chemical Science, 2018, vol. 9, # 21, p. 4756 - 4768
  • 34
  • [ 105-13-5 ]
  • [ 104146-10-3 ]
Reference: [1] Patent: CN107033162, 2017, A,
  • 35
  • [ 105-13-5 ]
  • [ 150308-80-8 ]
Reference: [1] Journal of Peptide Science, 2013, vol. 19, # 2, p. 65 - 73
  • 36
  • [ 68797-61-5 ]
  • [ 105-13-5 ]
  • [ 1325694-78-7 ]
YieldReaction ConditionsOperation in experiment
33% With potassium <i>tert</i>-butylate In tetrahydrofuran at 50℃; for 16 h; Inert atmosphere General procedure: To a mixture of dichloride 21 (0.625 g, 2.7 mmol) and potassium tert-butoxide (0.395 g, 4.1 mmol) was added a solution of para-methoxybenzyl alcohol (0.568 g, 4.1 mmol) in THF (8 mL). Reaction mixture was heated to 50 °C overnight. Reaction mixture was filtered and concentrated under reduced pressure. Product was purified via automated chromatography (EtOAc: Hexanes, 20:80) to provide 22 as a clear oil in 33percent yield. 1H NMR (400 MHz, CDCl3) δ 8.38 (s, 1H), 7.30 (d, J = 8.6 Hz, 1H), 6.83 (d, J = 8.6 Hz, 1H), 5.38 (s, 2H), 3.73 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 166.68, 160.23, 159.85, 155.22, 130.28, 130.16, 130.00, 127.24, 114.02, 106.27, 70.10, 55.32.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 15, p. 4592 - 4596
  • 37
  • [ 105-13-5 ]
  • [ 1384122-86-4 ]
Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 1, p. 9 - 34
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