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Product Details of [ 98-28-2 ]

CAS No. :98-28-2 MDL No. :MFCD00019992
Formula : C10H13ClO Boiling Point : -
Linear Structure Formula :- InChI Key :PRLINSMUYJWPBL-UHFFFAOYSA-N
M.W : 184.66 Pubchem ID :7380
Synonyms :

Safety of [ 98-28-2 ]

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
GHS Pictogram:

Application In Synthesis of [ 98-28-2 ]

* 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 [ 98-28-2 ]

[ 98-28-2 ] Synthesis Path-Downstream   1~87

  • 1
  • [ 110-85-0 ]
  • [ 98-28-2 ]
  • [ 103757-75-1 ]
YieldReaction ConditionsOperation in experiment
With formaldehyd
  • 2
  • [ 107-39-1 ]
  • [ 95-57-8 ]
  • [ 98-28-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; iron(III) chloride
  • 3
  • [ 527-69-5 ]
  • [ 98-28-2 ]
  • [ 101353-18-8 ]
YieldReaction ConditionsOperation in experiment
With magnesium; benzene
  • 4
  • [ 50-00-0 ]
  • [ 98-28-2 ]
  • [ 802-62-0 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; acetic acid
  • 5
  • [ 50-00-0 ]
  • [ 98-28-2 ]
  • [ 101876-79-3 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride Erwaermen des Reaktionsprodukts mit 2,4-Dichlor-phenol und AlCl3 in Tetrachloraethen;
  • 6
  • [ 4752-64-1 ]
  • [ 98-28-2 ]
  • 4'-<i>tert</i>-butyl-3,4,6,6'-tetrachloro-2,2'-methanediyl-di-phenol [ No CAS ]
  • 7
  • [ 821-06-7 ]
  • [ 98-28-2 ]
  • 1,4-bis-(4-<i>tert</i>-butyl-2-chloro-phenoxy)-but-2<i>t</i>-ene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide
  • 8
  • [ 598-49-2 ]
  • [ 98-54-4 ]
  • [ 98-28-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; acetic acid
  • 9
  • [ 31702-33-7 ]
  • [ 98-28-2 ]
  • [ 106381-19-5 ]
YieldReaction ConditionsOperation in experiment
With iron(III) chloride at 140℃;
  • 10
  • [ 98-54-4 ]
  • [ 98-28-2 ]
YieldReaction ConditionsOperation in experiment
95% With methanol; sulfuryl dichloride In dichloromethane Ambient temperature;
95% With SO2Cl2 In methanol; dichloromethane; water 7 4-tert-butyl-2-chloro-phenol Example 7 4-tert-butyl-2-chloro-phenol To a solution of 4-tert-butyl-phenol (40.0 g, 0.27 mol) and SO2Cl2 (37.5 g, 0.28 mol) in CH2Cl2 was added MeOH (9.0 g, 0.28 mol) at 0° C. After addition was complete, the mixture was stirred overnight at room temperature and then water (200 mL) was added. The resulting solution was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under vacuum. The residue was purified by column chromatography (Pet. Ether/EtOAc, 50:1) to give 4-tert-butyl-2-chloro-phenol (47.0 g, 95%).
95% With sulfuryl dichloride In methanol; dichloromethane at 0 - 20℃; 7 4-tert-butyl-2-chloro-phenol To a solution of 4-tert-butyl-phenol (40.0 g, 0.27 mol) and SO2Cl2 (37.5 g, 0.28 mol) in CH2Cl2 was added MeOH (9.0 g, 0.28 mol) at 0° C. After addition was complete, the mixture was stirred overnight at room temperature and then water (200 mL) was added. The resulting solution was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under vacuum. The residue was purified by column chromatography (Pet. Ether/EtOAc, 50:1) to give 4-tert-butyl-2-chlorophenol (47.0 g, 95%).
88% With 2,4,6-tris[(4-dichloroiodo)phenoxy]-1,3,5-triazine In acetonitrile at 20℃; for 2h; General Procedure for Nuclear Chlorination of Arenes General procedure: Reagent 8 (0.5 mmol) was added to a stirred solution of the appropiate activated arene (1 mmol) in CH2Cl2 (3 mL). The reaction mixture was stirred at r.t. for the period of timegiven in Table 1, and progress of reaction was monitored byTLC. When the substrate was consumed, the CH2Cl2 was evaporated under reduced pressure. MeOH was added to the reaction mass, and the white precipitate was isolated by filtration. The residue was washed several times with small aliquote of MeOH and air-dried to recover 2,4,6-tris(4-iodophenoxy)-1,3,5-triazine in 93% yield. The filtrate was concentrated in vacuo to afford the crude product which was purified by column chromatography on silica gel using PE-EtOAc (9:1) as eluent to give the chlorinated product in excellent purity.
83% With chloro-trimethyl-silane; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 18h; Inert atmosphere;
at 65 - 85℃; Einleiten von Chlor;
With sulfuryl dichloride In tetrachloromethane
With diisobutylamine; sulfuryl dichloride
With diisobutylamine; sulfuryl dichloride In toluene at 25℃; for 2h;
With sulfuryl dichloride In chloroform 1.a EXAMPLE 1 (a) To a stirred solution of 27.6 g. of 4-tert. butylphenol in 225 ml. of chloroform is added dropwise at 0 degrees C., 26.82 g. of sulfuryl chloride. The yellow solution is kept overnight at 5 degrees C. and the solvent and excess reagent are then removed in vacuo. The residue is distilled under reduced pressure to produce 27.2 g. of 4-tert.butyl-2-chlorophenol, b.p. 85-90 degrees C./1 mmHg.
With sulfuryl dichloride In dichloromethane 30.1.1 (Step 1-1) (Step 1-1) Synthesis of 2-chloro-4-t-butylphenol: 4-t-Butylphenol (2.76 g, 18.4 mmol) was dissolved in dichloromethane (25 ml). Sulfuryl chloride (1.6 ml, 9.9 mmol) was added dropwise to the obtained solution, and they were stirred at room temperature for 3 days and then concentrated under reduced pressure. After the purification by the silica gel column chromatography, 2-chloro-4-t-butylphenol (yield: 2.71 g, 80 %) was obtained. 1H-NMR(300MHz, CDCl3) δ =1.28(9H, s), 5.37(1H, s), 6.94(1H, d, J=8.6Hz), 7.19(1H, dd, J=8.6Hz, 2.5Hz), 7.30(1H, d, J=2.5Hz).
95 %Spectr. With (Dichloroiodo)benzene In acetonitrile at 20℃; for 8h;
33 %Chromat. With copper dichloride In acetic acid at 80℃; for 6h;

Reference: [1]Masilamani, Divakar; Rogic, Milorad M. [Journal of Organic Chemistry, 1981, vol. 46, # 22, p. 4486 - 4489]
[2]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - US2011/98311, 2011, A1 Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - US2012/309758, 2012, A1
[3]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - US2015/231142, 2015, A1 Location in patent: Paragraph 0519
[4]Thorat, Prerana B.; Bhong, Bhagyashree Y.; Karade, Nandkishor Y. [Synlett, 2013, vol. 24, # 16, p. 2061 - 2066]
[5]Granados, Albert; Jia, Zhiyu; del Olmo, Marc; Vallribera, Adelina [European Journal of Organic Chemistry, 2019, vol. 2019, # 17, p. 2812 - 2818]
[6]Current Patent Assignee: DOW INC - US2221807, 1934, A Current Patent Assignee: DOW INC - US2176010, 1935, A
[7]Kaemmerer,H.; Haberer,K. [Chemische Berichte, 1963, vol. 96, p. 2613 - 2616]
[8]Koyama, Hiroo; Boueres, Julia K.; Miller, Daniel J.; Berger, Joel P.; MacNaul, Karen L.; Wang, Pei-Ran; Ippolito, Marc C.; Wright, Samuel D.; Agrawal, Arun K.; Moller, David E.; Sahoo, Soumya P. [Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 14, p. 3347 - 3351]
[9]Shi, Guo Q.; Dropinski, James F.; Zhang, Yong; Santini, Conrad; Sahoo, Soumya P.; Berger, Joel P.; MacNaul, Karen L.; Zhou, Gaochao; Agrawal, Arun; Alvaro, Raul; Cai, Tian-Quan; Hernandez, Melba; Wright, Samuel D.; Moller, David E.; Heck, James V.; Meinke, Peter T. [Journal of Medicinal Chemistry, 2005, vol. 48, # 17, p. 5589 - 5599]
[10]Current Patent Assignee: ABBOTT LABORATORIES INC - US4312887, 1982, A
[11]Current Patent Assignee: EISAI CO LTD - EP1346993, 2003, A1
[12]Location in patent: body text Podgorsek, Ajda; Jurisch, Markus; Stavber, Stojan; Zupan, Marko; Iskra, Jernej; Gladysz, John A. [Journal of Organic Chemistry, 2009, vol. 74, # 8, p. 3133 - 3140]
[13]Su, Peigen; Fan, Chao; Yu, Heng; Wang, Wanqin; Jia, Xin; Rao, Qifan; Fu, Chenxi; Zhang, Donghua; Huang, Benhua; Pan, Cheng; Zheng, Aqun; Sun, Yang [Molecular catalysis, 2019, vol. 475]
  • 11
  • [ 98-28-2 ]
  • [ 17026-49-2 ]
  • 2,6-bis-(5-<i>tert</i>-butyl-3-chloro-2-hydroxy-benzyl)-4-chloro-phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; acetic acid
  • 12
  • [ 98-28-2 ]
  • [ 14593-28-3 ]
  • 13
  • [ 98-28-2 ]
  • [ 71730-43-3 ]
YieldReaction ConditionsOperation in experiment
With hexamethylenetetramine; boric acid; glycerol at 150 - 165℃; und Behandeln des Reaktionsgemisches mit wss.H2SO4 unter Durchleiten von Wasserdampf;
  • 14
  • [ 98-28-2 ]
  • [ 114097-52-8 ]
YieldReaction ConditionsOperation in experiment
With potassium chloride; phosphorus trichloride
With magnesium chloride; phosphorus trichloride
  • 15
  • [ 98-28-2 ]
  • [ 94074-84-7 ]
YieldReaction ConditionsOperation in experiment
With copper(l) chloride; magnesium chloride; trichlorophosphate
Multi-step reaction with 2 steps 1: MgCl2; PCl3 2: sulfur; PCl3 / Edukt 4: Thiophosphorsaeure-<i>O</i>-<4-<i>tert</i>-butyl-2-chlor-phenylester>-dichlorid
  • 16
  • [ 98-28-2 ]
  • [ 107-06-2 ]
  • [ 2051-63-0 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide
  • 17
  • [ 98-28-2 ]
  • [ 75-36-5 ]
  • [ 100388-76-9 ]
YieldReaction ConditionsOperation in experiment
With magnesium; benzene
  • 18
  • [ 98-28-2 ]
  • [ 111-44-4 ]
  • 1-(4-<i>tert</i>-butyl-2-chloro-phenoxy)-2-(2-chloro-ethoxy)-ethane [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; water at 107 - 110℃;
  • 19
  • [ 98-28-2 ]
  • [ 98-59-9 ]
  • [ 7598-31-4 ]
  • 20
  • [ 50-00-0 ]
  • [ 98-28-2 ]
  • [ 74-89-5 ]
  • bis-(5-<i>tert</i>-butyl-3-chloro-2-hydroxy-benzyl)-methyl-amine [ No CAS ]
  • 21
  • [ 95-57-8 ]
  • [ 115-11-7 ]
  • [ 98-28-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; iron(III) chloride
With trichlorophosphate
  • 22
  • [ 95-57-8 ]
  • [ 115-11-7 ]
  • [ 98-28-2 ]
  • [ 4237-37-0 ]
YieldReaction ConditionsOperation in experiment
With trichlorophosphate
  • 23
  • [ 98-28-2 ]
  • [ 127-00-4 ]
  • 1-(4-<i>tert</i>-butyl-2-chloro-phenoxy)-propan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide
  • 24
  • [ 98-28-2 ]
  • [ 110-75-8 ]
  • 1-(4-<i>tert</i>-butyl-2-chloro-phenoxy)-2-vinyloxy-ethane [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide at 150℃;
  • 25
  • [ 98-28-2 ]
  • [ 107-07-3 ]
  • [ 56949-55-4 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide
  • 26
  • [ 95-57-8 ]
  • [ 75-65-0 ]
  • [ 98-28-2 ]
YieldReaction ConditionsOperation in experiment
With Fuller's Earth at 150℃;
  • 27
  • 2-ethoxyvinylphosphonyl dichloride [ No CAS ]
  • [ 98-28-2 ]
  • [ 41842-94-8 ]
YieldReaction ConditionsOperation in experiment
With pyridine In benzene
  • 28
  • [ 6698-56-2 ]
  • [ 98-28-2 ]
  • C14H19Cl2O2PS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine In toluene
  • 30
  • [ 98-28-2 ]
  • [ 42069-07-8 ]
  • [ 33348-28-6 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In benzene
  • 31
  • [ 98-28-2 ]
  • [ 76907-92-1 ]
  • [ 33348-30-0 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In benzene
  • 32
  • [ 98-28-2 ]
  • Thiophosphorochloridic acid O-ethyl ester S-(2-propoxy-ethyl) ester [ No CAS ]
  • [ 33348-29-7 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In benzene
  • 33
  • [ 98-28-2 ]
  • [ 7651-98-1 ]
  • [ 38524-57-1 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In benzene
  • 34
  • [ 98-28-2 ]
  • [ 127-06-0 ]
  • [ 676-98-2 ]
  • [ 34694-01-4 ]
YieldReaction ConditionsOperation in experiment
(i) KOtBu, THF, (ii) /BRN= 969370/, (iii) /BRN= 2043336/; Multistep reaction;
With sodium hydroxide In tetrahydrofuran
  • 35
  • [ 50-00-0 ]
  • [ 98-28-2 ]
  • [ 80626-06-8 ]
YieldReaction ConditionsOperation in experiment
81% With hydrogenchloride at 20℃; for 16h;
  • 36
  • [ 2832-19-1 ]
  • [ 98-28-2 ]
  • 2-(4-tert-Butyl-2-chloro-phenoxy)-N-hydroxymethyl-acetamide [ No CAS ]
  • 37
  • [ 2832-19-1 ]
  • [ 98-28-2 ]
  • N-(5-tert-Butyl-3-chloro-2-hydroxy-benzyl)-2-chloro-acetamide [ No CAS ]
  • 39
  • [ 98-28-2 ]
  • [ 76-05-1 ]
  • [ 71730-43-3 ]
YieldReaction ConditionsOperation in experiment
29% With hexamethylenetetramine at 83 - 90℃; for 8h;
  • 40
  • [ 98-28-2 ]
  • 5-t-butyl-2,1,3-benzothiadiazole [ No CAS ]
  • 6-t-butyl-4-chloro-2,1,3-benzothiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 56 % Chromat. 2: 40 % Chromat. With N4S4 In toluene for 24h; Heating;
  • 41
  • [ 50-00-0 ]
  • [ 98-28-2 ]
  • [ 16396-75-1 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide
  • 42
  • [ 98-28-2 ]
  • [ 15516-32-2 ]
YieldReaction ConditionsOperation in experiment
With 5-chloro-1-ethyl-2-methyl-1H-imidazole; trichlorophosphate at 150℃;
  • 43
  • [ 98-28-2 ]
  • [ 908-17-8 ]
  • [ 916-24-5 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In ethanol
  • 44
  • [ 98-28-2 ]
  • [ 16396-75-1 ]
  • [ 802-62-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In ethanol
  • 45
  • [ 50-00-0 ]
  • [ 98-28-2 ]
  • bis[3-chloro-2-hydroxy-5-(1,1-dimethylethyl)benzenemethanolato(2-)-O,O']borate(1-) sodium salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With sodium hydroxide; boric acid In water at 50℃; for 24h;
  • 48
  • [ 98-28-2 ]
  • [ 16555-77-4 ]
  • benzoylamino-(5-<i>tert</i>-butyl-3-chloro-2-hydroxy-phenyl)-acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid In acetic acid at 20℃;
  • 49
  • [ 98-28-2 ]
  • amino-(5-<i>tert</i>-butyl-3-chloro-2-hydroxy-phenyl)-acetic acid; hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: H2SO4 / acetic acid / 20 °C 2: aq. HCl / Heating
  • 50
  • [ 98-28-2 ]
  • [ 883967-51-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Cs2CO3 / dimethylformamide / 5 h / 60 °C 2: triphenylphosphine; imidazole; iodine / CH2Cl2 / 1 h / 25 °C
  • 51
  • [ 98-28-2 ]
  • 5-[3-(4-<i>tert</i>-butyl-2-chloro-phenoxy)-propoxy]-2-ethyl-2,3-dihydro-benzofuran-2-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Cs2CO3 / dimethylformamide / 5 h / 60 °C 2: triphenylphosphine; imidazole; iodine / CH2Cl2 / 1 h / 25 °C 3: Cs2CO3 / dimethylformamide / 6 h / 25 °C
  • 52
  • [ 98-28-2 ]
  • 5-[3-(4-<i>tert</i>-butyl-2-chloro-phenoxy)-propoxy]-2-ethyl-2,3-dihydro-benzofuran-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: Cs2CO3 / dimethylformamide / 5 h / 60 °C 2: triphenylphosphine; imidazole; iodine / CH2Cl2 / 1 h / 25 °C 3: Cs2CO3 / dimethylformamide / 6 h / 25 °C 4: aq. KOH / methanol / 3 h / 25 - 60 °C
  • 54
  • [ 98-28-2 ]
  • 7-[3-(4-<i>tert</i>-butyl-2-chloro-phenoxy)-propoxy]-2-methyl-chroman-2-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Cs2CO3 2: Cs2CO3 / dimethylformamide / 65 °C
  • 55
  • [ 98-28-2 ]
  • (2R)-7-(3-(2-Chloro-4-tert-butylphenoxy)propoxy)-2-methylchromane-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Cs2CO3 2: Cs2CO3 / dimethylformamide / 65 °C 3: aq. NaOH / propan-2-ol / 12 h / 70 °C
  • 56
  • [ 98-28-2 ]
  • 7-[3-(4-<i>tert</i>-butyl-2-chloro-phenoxy)-propoxy]-2-ethyl-chroman-2-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Cs2CO3 2: Cs2CO3 / dimethylformamide / 65 °C
  • 57
  • [ 98-28-2 ]
  • (2R)-7-(3-(2-Chloro-4-tert-butylphenoxy)propoxy)-2-ethylchromane-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Cs2CO3 2: Cs2CO3 / dimethylformamide / 65 °C 3: aq. NaOH / propan-2-ol / 12 h / 70 °C
  • 58
  • [ 98-28-2 ]
  • [ 38946-43-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: conc. H2SO4, HOAc / 16 h / 22 °C 2: conc. HCl / ethanol / 1.5 h / Heating
  • 59
  • [ 98-28-2 ]
  • [ 78335-95-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 29 percent / hexamethylenetetramine / 8 h / 83 - 90 °C 2: 51 percent / benzene / 4 h / Heating 3: 45 percent / H2SO4, H2 / 5percent Rh/Cd / ethanol / 20 h / 1448.01 Torr
  • 60
  • [ 98-28-2 ]
  • 3-<3-chloro-5-(1,1-dimethylethyl)-2-hydroxyphenyl>propenenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 29 percent / hexamethylenetetramine / 8 h / 83 - 90 °C 2: 51 percent / benzene / 4 h / Heating
  • 61
  • [ 98-28-2 ]
  • [ 81440-79-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: conc. H2SO4 / acetic acid / 4 h / 22 °C 2: NaI / acetone / 0.25 h / Heating 3: K2CO3 / dimethylformamide / 1.5 h / 65 °C
  • 62
  • [ 98-28-2 ]
  • 2-(4-tert-Butyl-2-chloro-phenoxy)-N-iodomethyl-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: conc. H2SO4 / acetic acid / 4 h / 22 °C 2: NaI / acetone / 0.25 h / Heating
  • 63
  • [ 98-28-2 ]
  • [ 81440-77-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 81 percent / conc. HCl / 16 h / 20 °C 2: dimethylformamide / 1 h / 20 °C
  • 64
  • [ 98-28-2 ]
  • [ 81440-78-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 81 percent / conc. HCl / 16 h / 20 °C 2: dimethylformamide / 1 h / 20 °C
  • 65
  • [ 98-28-2 ]
  • [ 150936-97-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: conc. H2SO4 / acetic acid / 4 h / 22 °C 2: NaI / acetone / 0.25 h / Heating 3: K2CO3 / dimethylformamide / 1.5 h / 65 °C 4: Red Al / benzene / 2.5 h / Heating
  • 66
  • [ 98-28-2 ]
  • 5-<i>tert</i>-butyl-3-chloro-2-hydroxy-benzaldehyde phenylhydrazone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hexamethylenetetramine; glycerol; boric acid / 150 - 165 °C / und Behandeln des Reaktionsgemisches mit wss.H2SO4 unter Durchleiten von Wasserdampf
  • 67
  • [ 98-28-2 ]
  • <i>N</i>,<i>N</i>'-bis-(5-<i>tert</i>-butyl-3-chloro-2-hydroxy-benzyliden)-ethylenediamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hexamethylenetetramine; glycerol; boric acid / 150 - 165 °C / und Behandeln des Reaktionsgemisches mit wss.H2SO4 unter Durchleiten von Wasserdampf
  • 68
  • [ 98-28-2 ]
  • acetic acid-(4-<i>tert</i>-butyl-2-chloro-6-nitro-phenyl ester) [ No CAS ]
  • 69
  • [ 98-28-2 ]
  • [ 651430-57-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzene; magnesium 2: aluminium chloride; carbon disulfide / 110 °C
  • 70
  • [ 98-28-2 ]
  • (5-<i>tert</i>-butyl-3-chloro-2-hydroxy-phenyl)-[2]furyl ketone-(2,4-dinitro-phenylhydrazone) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: benzene; magnesium 2: aluminium chloride; carbon disulfide / 110 °C
  • 71
  • [ 98-28-2 ]
  • [ 41842-96-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Py / benzene 2: benzene
  • 72
  • [ 98-28-2 ]
  • C15H23ClNO2PS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Py / toluene 2: benzene
  • 73
  • [ 98-28-2 ]
  • [ 69919-18-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: POCl3, 5-chloro-1-ethyl-2-methyl-1H-imidazole / 150 °C 2: 5-chloro-1-ethyl-2-methyl-1H-imidazole / dioxane / 150 °C
  • 74
  • [ 98-28-2 ]
  • [ 6638-87-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aq. NaOH 2: H2, KOH / Raney-Ni / methanol
  • 75
  • 1-amidino-4-piperidinopropionic acid hydrochloride [ No CAS ]
  • [ 98-28-2 ]
  • [ 84511-39-7 ]
YieldReaction ConditionsOperation in experiment
With pyridine; thionyl chloride In <i>N</i>-methyl-acetamide 14 2'-Chloro-4'-t-butylphenyl 1-amidino-4-piperidinepropionate hydrochloride EXAMPLE 14 2'-Chloro-4'-t-butylphenyl 1-amidino-4-piperidinepropionate hydrochloride 5.3 g bis-(2-chloro-4-t-butylphenyl)sulfite prepared from 2-chloro-4-t-butylphenol and thionyl chloride was dissolved in a solution of 16 ml of dry dimethylformamide end 8 ml of dry pyridine, and 2.0 g of 1-amidino-4-piperidinepropionic acid hydrochloride was added with stirring to the resulting solution, and the mixture was stirred at room temperature for 2 hours.
  • 76
  • [ 98-28-2 ]
  • [ 63349-50-8 ]
  • [ 63350-04-9 ]
YieldReaction ConditionsOperation in experiment
With potassium iodide; sodium methylate In methanol; benzene 69 Methyl α-(2-chloro-4-tert-butylphenoxy)-α-[p-(p-chlorophenoxy)phenyl]acetate EXAMPLE 69 Methyl α-(2-chloro-4-tert-butylphenoxy)-α-[p-(p-chlorophenoxy)phenyl]acetate To a solution of 4.62 g of 2-chloro-4-tert-butylphenol, 1.188 g of sodium methoxide and 50 mg of potassium iodide in 40 ml of methanol is added 7.11 g of methyl α-bromo-α-[p-(p-chlorophenoxy)phenyl]acetate in 10 ml of benzene. The mixture is heated at reflux overnight. The mixture is worked up as described in Example 68 to yield a yellow oil. Chromatography on 100 g of silica gel (benzene, 400 ml) affords an oil which solidifies. Recrystallization from hexane yields white plates, mp 85.5°-88° C.
  • 77
  • [ 50-00-0 ]
  • [ 98-28-2 ]
  • [ 11113-50-1 ]
  • [ 1310-73-2 ]
  • bis[3-chloro-2-hydroxy-5-(1,1-dimethylethyl)benzenemethanolato(2-)-O,O']borate(1-) sodium salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% In water stirring substituted phenol with 37% aq. HCHO at 50°C, addn. of H3BO3 and NaOH, stirring for 24 h (crystn.); slow cooling to room temp., water addn., stirring, collection (filtration), washing (water, hexanes), drying (desiccator);
  • 78
  • [ 161988-49-4 ]
  • [ 98-28-2 ]
  • [ 1078600-03-9 ]
YieldReaction ConditionsOperation in experiment
77% Stage #1: ethyl 6-(bromomethyl)-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate; 2-chloro-4-tert-butylphenol With ethanol; sodium for 2h; Reflux; Stage #2: With potassium hydroxide In ethanol; water for 2h; Reflux;
  • 79
  • [ 98-28-2 ]
  • [ 79-22-1 ]
  • [ 28188-66-1 ]
YieldReaction ConditionsOperation in experiment
92% With dmap; triethylamine In dichloromethane 7 4-tert-Butyl-2-chlorophenyl methyl carbonate 4-tert-Butyl-2-chlorophenyl methyl carbonate To a solution of 4-tert-butyl-2-chlorophenol (47.0 g, 0.25 mol) in dichloromethane (200 mL) was added Et3N (50.5 g, 0.50 mol), DMAP (1 g) and methyl chloroformate (35.4 g, 0.38 mol) at 0° C. The reaction was allowed to warm to room temperature and stirred for additional 30 min. The reaction mixture was washed with H2O and the organic layer was dried over Na2SO4 and concentrated to give 4-tert-butyl-2-chlorophenyl methyl carbonate (56.6 g, 92%), which was used directly in the next step.
92% With dmap; triethylamine In dichloromethane at 0 - 20℃; for 0.5h; 7 4-tert-Butyl-2-chlorophenyl methyl carbonate To a solution of 4-tert-butyl-2-chlorophenol (47.0 g, 0.25 mol) in dichloromethane (200 mL) was added Et3N (50.5 g, 0.50 mol), DMAP (1 g) and methyl chloroformate (35.4 g, 0.38 mol) at 0° C. The reaction was allowed to warm to room temperature and stirred for additional 30 min. The reaction mixture was washed with H2O and the organic layer was dried over Na2SO4 and concentrated to give 4-tert-butyl-2-chlorophenyl methyl carbonate (56.6 g, 92%), which was used directly in the next step.
  • 80
  • [ 98-28-2 ]
  • [ 873055-59-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap; triethylamine / dichloromethane 2: KNO3 / sulfuric acid
Multi-step reaction with 2 steps 1: dmap; triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 2: sulfuric acid; potassium nitrate / 1.92 h / 0 °C
  • 81
  • [ 98-28-2 ]
  • [ 873055-60-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dmap; triethylamine / dichloromethane 2: KNO3 / sulfuric acid 3: potassium hydroxide / methanol
Multi-step reaction with 3 steps 1: dmap; triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 2: sulfuric acid; potassium nitrate / 1.92 h / 0 °C 3: potassium hydroxide / methanol / 0.5 h
  • 82
  • [ 98-28-2 ]
  • [ 873055-61-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: dmap; triethylamine / dichloromethane 2: KNO3 / sulfuric acid 3: potassium hydroxide / methanol 4: methanol
Multi-step reaction with 4 steps 1: dmap; triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 2: sulfuric acid; potassium nitrate / 1.92 h / 0 °C 3: potassium hydroxide / methanol / 0.5 h 4: hydrogen; nickel / methanol / 4 h / 760.05 Torr
  • 83
  • [ 98-28-2 ]
  • cis-3-[(pyrazolo[1,5-a]pyridin-3-ylcarbonyl)amino]cyclobutyl methanesulfonate [ No CAS ]
  • N-(trans-3-([2-chloro-4-(1,1-dimethylethyl)phenyl]oxy)cyclobutyl)pyrazolo[1,5-a]pyridine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 70℃; 7 Example 7: A/-( ra/7s-3-{r2-Chloro-4-(1 , 1-dimethylethyl)phenylloxy)cvclobutyl)pyrazolori ,5- al pyri d i n e- 3- carboxa m i deA mixture of c/'s-3-[(pyrazolo[1 ,5-a]pyridin-3-ylcarbonyl)amino]cyclobutyl methanesulfonate (73 mg, 0.236 mmol), 2-chloro-4-(1 , 1-dimethylethyl)phenol (43.6 mg, 0.236 mmol) and potassium tert-butoxide (53.0 mg, 0.472 mmol) in Ν, Ν-dimethylformamide (DMF) (3.00 ml_) was heated at 70°C for 3 h. Additional potassium tert-butoxide (53.0 mg, 0.472 mmol) was added and the reaction was stirred at 70 °C over the weekend. The reaction was concentrated in vacuo. The crude product was purified by Mass Directed HPLC (Method B) and fractions which contain product were concentrated to give the title compound.LC-MS (System B) rt = 3.35min, MH+ = 378
  • 84
  • [ 98-28-2 ]
  • [ 693-02-7 ]
  • [ 98-54-4 ]
  • [ 1388142-03-7 ]
YieldReaction ConditionsOperation in experiment
1: 59% 2: 10 %Chromat. In water; acetone; acetonitrile for 32h; Inert atmosphere; Photolysis;
  • 85
  • [ 98-28-2 ]
  • [ 1066-54-2 ]
  • [ 98-54-4 ]
  • [ 1388142-04-8 ]
YieldReaction ConditionsOperation in experiment
1: 65% 2: 11 %Chromat. In water; acetone; acetonitrile for 32h; Inert atmosphere; Photolysis;
  • 86
  • [ 98-28-2 ]
  • [ 126334-84-7 ]
  • C29H28ClNO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In acetonitrile Reflux;
  • 87
  • [ 98-28-2 ]
  • [ 626216-36-2 ]
  • [ 1392198-00-3 ]
YieldReaction ConditionsOperation in experiment
51.8% With 1,3,5-Trioxan In ethanol for 12h; Inert atmosphere; Schlenk technique; Reflux;
Same Skeleton Products
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