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Product Details of [ 768-95-6 ]

CAS No. :768-95-6 MDL No. :MFCD00074729
Formula : C10H16O Boiling Point : -
Linear Structure Formula :- InChI Key :VLLNJDMHDJRNFK-UHFFFAOYSA-N
M.W : 152.23 Pubchem ID :64152
Synonyms :

Calculated chemistry of [ 768-95-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.04
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.71 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.12
Log Po/w (XLOGP3) : 2.14
Log Po/w (WLOGP) : 1.95
Log Po/w (MLOGP) : 2.45
Log Po/w (SILICOS-IT) : 2.15
Consensus Log Po/w : 2.16

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.13
Solubility : 1.12 mg/ml ; 0.00738 mol/l
Class : Soluble
Log S (Ali) : -2.2
Solubility : 0.968 mg/ml ; 0.00636 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.35
Solubility : 6.74 mg/ml ; 0.0443 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.69

Safety of [ 768-95-6 ]

Signal Word:Danger Class:4.1
Precautionary Statements:P240-P210-P264-P280-P370+P378-P337+P313 UN#:1325
Hazard Statements:H315-H319-H335-H228 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 768-95-6 ]

* 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 [ 768-95-6 ]
  • Downstream synthetic route of [ 768-95-6 ]

[ 768-95-6 ] Synthesis Path-Upstream   1~42

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Reference: [1] Bulletin of the Chemical Society of Japan, 1992, vol. 65, # 3, p. 846 - 852
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Reference: [1] Justus Liebigs Annalen der Chemie, 1972, vol. 766, p. 51 - 57
  • 3
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Reference: [1] Angewandte Chemie, 1965, vol. 77, p. 967
[2] Chemische Berichte, 1968, vol. 101, p. 564 - 573
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  • [ 20098-14-0 ]
Reference: [1] Patent: US6429314, 2002, B1,
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Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1983, p. 297 - 300[2] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 2, p. 339 - 343
[3] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1981, vol. 30, # 12, p. 2370[4] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1981, # 12, p. 2839
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  • [ 768-91-2 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1983, p. 297 - 300[2] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 2, p. 339 - 343
  • 7
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  • [ 768-90-1 ]
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Reference: [1] J. Gen. Chem. USSR (Engl. Transl.), 1991, vol. 61, # 10, p. 2190 - 2191[2] Zhurnal Obshchei Khimii, 1991, vol. 61, # 10, p. 2360 - 2361
  • 8
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YieldReaction ConditionsOperation in experiment
38% With oxygen In acetic acid tert-butyl ester at 100℃; for 96 h; The procedure of Example 1 was repeated, except that the catalyst was replaced by a catalyst that vanadium (18 μmol) is supported on montmorillonite (i.e., a V/Mont. catalyst); the amount of adamantane employed was changed to 3 mmol; t-butyl acetate was employed as a solvent; and reaction was performed at 100° C. for 96 hours. The V/Mont. catalyst was formed through the catalyst preparation process described in Japanese Patent Application Laid-Open (kokai) No. 2004-2234. Specifically, the catalyst was obtained by adding an aqueous vanadium(III) chloride solution to montmorillonite (Kunipia F, product of Kunimine Industries Co., Ltd.), followed by ion exchange, filtration, washing with water, drying, and firing in air at 800° C.
Reference: [1] Journal of the American Chemical Society, 1989, vol. 111, # 17, p. 6749 - 6757
[2] Journal of the American Chemical Society, 2005, vol. 127, # 44, p. 15391 - 15393
[3] Tetrahedron Letters, 1999, vol. 40, # 11, p. 2165 - 2168
[4] Tetrahedron Letters, 1999, vol. 40, # 11, p. 2165 - 2168
[5] Patent: US2006/235245, 2006, A1, . Location in patent: Page/Page column 6-7
[6] Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4520 - 4526
[7] Tetrahedron Letters, 1996, vol. 37, # 28, p. 4993 - 4996
[8] Journal of the American Chemical Society, 1989, vol. 111, # 17, p. 6749 - 6757
[9] Journal of the American Chemical Society, 1992, vol. 114, # 26, p. 10660 - 10662
[10] Heterocycles, 1995, vol. 40, # 2, p. 867 - 904
[11] Journal of the American Chemical Society, 1989, vol. 111, # 17, p. 6749 - 6757
[12] Tetrahedron Letters, 1996, vol. 37, # 28, p. 4993 - 4996
[13] Journal of Organic Chemistry, 2000, vol. 65, # 26, p. 9186 - 9193
[14] Chemical Communications, 2001, # 2, p. 191 - 192
[15] Chemistry Letters, 2005, vol. 34, # 12, p. 1626 - 1627
[16] Journal of Organic Chemistry, 2000, vol. 65, # 26, p. 9186 - 9193
[17] Chemistry - A European Journal, 2006, vol. 12, # 12, p. 3401 - 3409
[18] Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2258 - 2265
[19] Journal of the American Chemical Society, 2011, vol. 133, # 21, p. 8074 - 8077
[20] Chemistry - A European Journal, 2013, vol. 19, # 43, p. 14697 - 14701
  • 9
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YieldReaction ConditionsOperation in experiment
52% With manganese(IV) oxide; N-hydroxyphthalimide; oxygen; cobalt acetylacetonate In acetic acid at 60℃; for 30 h; A mixture of 25 g (0.164 mol) of 1-adamantanol I, 2.68 g (0.0164 mol) of NHPI, 0.482 g (1.64 mmol) of Co(acac)2, 0.715 g (0.0082 mol) of MnO2, and 250 mL of glacial acetic acid was heated under vigorous stirring to 60°C and then stirred at that temperature upon stirring and bubbling with oxygen during 30 h. After cooling, acetic acid was removed. The residue was dissolved in 250 mL of chloroform and heated at reflux during 2 h. Solid adamantane-1,3,5-triol III was filtered off and recrystallized from ethyl acetate. Yield 15.7 g (52 percent), mp 202–204°C (mp 203–205°C [17]). Adamantane-1,3-diol II precipitated from chloroform was filtered off and dried. Yield 10.7 g (39 percent), mp 296–297°C (mp 298–300°C [26]). Mass spectrum, m/z (Irel, percent): 1, 152 (35) [M]+, 109 (10), 95(100); II, 168 (28) [M]+, 150 (4), 111 (100), 95 (14);III, 184 (10) [M]+, 166 (6), 150 (50), 127 (100), 111(46), 92 (28).
Reference: [1] Russian Journal of General Chemistry, 2015, vol. 85, # 8, p. 1830 - 1833[2] Zh. Obshch. Khim., 2015, vol. 85, # 8, p. 1271 - 1275,5
  • 10
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YieldReaction ConditionsOperation in experiment
25% at 75℃; for 6 h; The procedure of Example 1 was repeated, except that the catalyst was replaced by NHPI (1 mmol) and VO(acac)2 (50 μmol); the amount of acetic acid serving as a solvent was changed to 25 mL; and the reaction temperature was changed to 75° C.
Reference: [1] Tetrahedron Letters, 1990, vol. 31, # 21, p. 3067 - 3070
[2] Journal of the American Chemical Society, 2002, vol. 124, # 47, p. 13978 - 13979
[3] Organic Letters, 2014, vol. 16, # 24, p. 6504 - 6507
[4] Tetrahedron Letters, 1999, vol. 40, # 11, p. 2165 - 2168
[5] Synthetic Communications, 1996, vol. 26, # 8, p. 1555 - 1562
[6] Chemical Communications, 2004, # 7, p. 798 - 799
[7] Chemistry - A European Journal, 2015, vol. 21, # 44, p. 15564 - 15569
[8] Patent: US2006/235245, 2006, A1, . Location in patent: Page/Page column 6-7
[9] Tetrahedron Letters, 1990, vol. 31, # 21, p. 3067 - 3070
[10] Journal of the American Chemical Society, 1996, vol. 118, # 37, p. 8961 - 8962
[11] Tetrahedron Letters, 1990, vol. 31, # 21, p. 3067 - 3070
[12] Journal of the American Chemical Society, 1992, vol. 114, # 4, p. 1346 - 1351
[13] Organic Letters, 2005, vol. 7, # 2, p. 263 - 266
[14] Patent: US6403521, 2002, B1,
[15] Organic and Biomolecular Chemistry, 2012, vol. 10, # 15, p. 3122 - 3130
[16] Chemistry - A European Journal, 2013, vol. 19, # 43, p. 14697 - 14701
[17] RSC Advances, 2016, vol. 6, # 96, p. 93756 - 93767
[18] Chemistry - An Asian Journal, 2018, vol. 13, # 17, p. 2458 - 2464
  • 11
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YieldReaction ConditionsOperation in experiment
11.4% at 120℃; for 6 h; The procedure of Example 6 was repeated, except that the amount of the catalyst was changed to 10 μmol, and the adamantane was replaced by 1-adamantanol (5 mmol).
Reference: [1] Synthetic Communications, 1996, vol. 26, # 8, p. 1555 - 1562
[2] Russian Journal of Organic Chemistry, 2009, vol. 45, # 8, p. 1137 - 1142
[3] Heterocycles, 1995, vol. 40, # 2, p. 867 - 904
[4] Organic Letters, 2017, vol. 19, # 18, p. 4790 - 4793
[5] Patent: US5958821, 1999, A,
[6] Patent: US2006/235245, 2006, A1, . Location in patent: Page/Page column 6-7
[7] Patent: US5958821, 1999, A,
[8] Journal of Organic Chemistry, 1995, vol. 60, # 17, p. 5673 - 5677
[9] Collection of Czechoslovak Chemical Communications, 1978, vol. 43, p. 3179 - 3191
[10] Tetrahedron, 1968, vol. 24, p. 5369 - 5377
[11] Journal of Organic Chemistry, 1995, vol. 60, # 17, p. 5673 - 5677
[12] Patent: EP1775296, 2007, A1, . Location in patent: Page/Page column 10; 10-11; 18; 19
[13] Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2258 - 2265
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YieldReaction ConditionsOperation in experiment
31.6% at 120℃; for 6 h; The procedure of Example 1 was repeated, except that the acetic acid serving as a solvent was replaced by propionic acid.
Example 7 The procedure of Example 6 was repeated, except that the amount of the catalyst was changed to 10 μmol.
Example 8 The procedure of Example 6 was repeated, except that the amount of the catalyst was changed to 1.3 μmol.
25.1% at 100℃; for 6 h; The procedure of Example 9 was repeated, except that methanesulfonic acid [CH3SO3H] was added in an amount of 0.004 mL.
23.2% at 100℃; for 6 h; The procedure of Example 9 was repeated, except that europium triflate [Eu(OTf)3] was added in an amount of 10 μmol.
21.7% at 110℃; for 6 h; The procedure of Example 6 was repeated, except that the amount of adamantane employed was changed to 5 mmol, and the catalyst was replaced by Co(acac)2.2H2O.
15.3% at 120℃; for 6 h; The procedure of Example 1 was repeated, except that the catalyst was replaced by a vanadium oxide-TPP complex [VOTPP].
15.5% at 100℃; for 6 h; The procedure of Example 6 was repeated, except that the amount of adamantane employed was changed to 5 mmol, and the reaction temperature was changed to 100° C.

Reference: [1] Chemical Communications, 2018, vol. 54, # 50, p. 6772 - 6775
[2] Patent: US2006/235245, 2006, A1, . Location in patent: Page/Page column 5-7
[3] Patent: US2006/235245, 2006, A1, . Location in patent: Page/Page column 6-7
[4] Patent: US2006/235245, 2006, A1, . Location in patent: Page/Page column 6-7
[5] Patent: US2006/235245, 2006, A1, . Location in patent: Page/Page column 6-7
[6] Patent: US2006/235245, 2006, A1, . Location in patent: Page/Page column 5-7
[7] Patent: US2006/235245, 2006, A1, . Location in patent: Page/Page column 6-7
[8] Tetrahedron Letters, 1995, vol. 36, # 44, p. 8059 - 8062
[9] Journal of Catalysis, 2005, vol. 233, # 1, p. 81 - 89
[10] Chemistry Letters, 2005, vol. 34, # 11, p. 1486 - 1487
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Reference: [1] Patent: EP1191010, 2002, A2, . Location in patent: Page column 5-7
[2] Synthetic Communications, 2013, vol. 43, # 8, p. 1161 - 1167
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YieldReaction ConditionsOperation in experiment
22.3% at 120℃; for 6 h; The procedure of Example 1 was repeated, except that the catalyst was replaced by acetylacetonatovanadium [V(acac)3].
18% at 120℃; for 6 h; Adamantane (10 mmol, 1.36 g) and acetylacetonatovanadyl [VO(acac)2] (5 μmol, 1.3 mg) serving as a catalyst were dissolved in acetic acid (10 mL) placed in a three-neck flask, and oxygen (1 atm) was continuously blown into the flask at a flow rate of 10 mL/min under stirring with a stirrer, to thereby allow partial oxidation of adamantane (ADM) to proceed for six hours at 120° C. The resultant product was subjected to quantitative analysis by means of a gas chromatograph, and as a result, the product was found to contain 1-adamantanol (1-AdOH), 2-adamantanol (2-AdOH), 1,3-adamantanediol (1,3-(AdOH)2), acetic acid esters of them, and 2-adamantanone (2-Ad=O). In the case of this product, adamantane conversion, total yield, and turnover number (TON) were found to be 37.0percent, 25.8percent, and 517, respectively. The results are shown in Table 1. Table 1 also shows analysis results for the cases of the below-described Examples and Referential Examples. As used herein, the turnover number is obtained by use of the following equation: [amount (mol) of adamantane consumed through reaction/amount (mol) of active metal (e.g., vanadium or cobalt) contained in the employed catalyst]. The greater the turnover number, the higher the reaction rate.
Example 2 The procedure of Example 1 was repeated, except that the amount of adamantane employed was changed to 5 mmol.
10.1% at 120℃; for 6 h; The procedure of Example 1 was repeated, except that the catalyst was replaced by ammonium metavanadate [NH4VO3].
Reference: [1] Patent: US2006/235245, 2006, A1, . Location in patent: Page/Page column 5-7
[2] Patent: US2006/235245, 2006, A1, . Location in patent: Page/Page column 5-7
[3] Patent: US2006/235245, 2006, A1, . Location in patent: Page/Page column 5-7
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Reference: [1] Applied Catalysis A: General, 2018, vol. 560, p. 171 - 184
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Reference: [1] Chemical Communications, 1996, # 15, p. 1833 - 1834
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  • [ 772-26-9 ]
Reference: [1] Russian Journal of Organic Chemistry, 2009, vol. 45, # 8, p. 1137 - 1142
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Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 43, p. 14697 - 14701
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Reference: [1] Catalysis Today, 2012, vol. 185, # 1, p. 157 - 161
[2] Chemistry - A European Journal, 2013, vol. 19, # 43, p. 14697 - 14701
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Reference: [1] Russian Journal of Organic Chemistry, 2007, vol. 43, # 4, p. 623 - 624
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Reference: [1] Russian Journal of Organic Chemistry, 2017, vol. 53, # 7, p. 971 - 976[2] Zh. Org. Khim., 2017, vol. 53, # 7, p. 959 - 964,5
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Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 2, p. 249 - 252
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Reference: [1] Russian Journal of Organic Chemistry, 2007, vol. 43, # 4, p. 623 - 624
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Reference: [1] Journal of Fluorine Chemistry, 1983, vol. 23, p. 502
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1996, # 9, p. 1811 - 1820
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Reference: [1] Tetrahedron Letters, 1990, vol. 31, # 21, p. 3067 - 3070
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Reference: [1] Tetrahedron Letters, 1990, vol. 31, # 21, p. 3067 - 3070
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Reference: [1] Russian Journal of Organic Chemistry, 2003, vol. 39, # 12, p. 1806 - 1808
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Reference: [1] Russian Journal of Organic Chemistry, 2003, vol. 39, # 12, p. 1806 - 1808
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Reference: [1] Patent: JP2016/84315, 2016, A,
  • 32
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Reference: [1] Chemische Berichte, 1968, vol. 101, p. 564 - 573
[2] Chemische Berichte, 1968, vol. 101, p. 564 - 573
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Reference: [1] Polyhedron, 2018, vol. 145, p. 141 - 146
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  • [ 106685-40-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 26, p. 4993 - 5006
[2] Bioorganic Chemistry, 2011, vol. 39, # 4, p. 151 - 158
[3] Patent: WO2007/125542, 2007, A2,
[4] Patent: WO2007/125542, 2007, A2,
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YieldReaction ConditionsOperation in experiment
97% at 70℃; for 3 h; Example 1; <n="15"/>Preparation of 2-(l-adamantyl)-4-bromophenol (III): A mixture of p-bromophenol (10.0 g, 57.8mmol) and 1-adamantanol (8.78 g, 57.76 mmol) in methane sulphonic acid (15 ml) was stirred for 3 h at 700C. The reaction mixture was cooled and diluted with water (50 ml). The white solid obtain was filtered, washed with water and dried. [Yield: 17 g, 97 percent]
90% at 20 - 70℃; for 4.16667 h; Example 3; Preparation of 2-(l-adamantyl)-4-bromophenol (III): A mixture of p-bromophenol (10.0 g, 57.8 mmol) and 1-adamantanol (8.78 g, 57.76 mmol) in acetic acid (20 ml) was stirred at room temperature. Then concentrated sulphuric acid (3.0 ml) was added in dropwise manner for 10 min. The reaction mixture was stirred for 4 h at 7O0C. The reaction mixture was cooled and diluted with water (50 ml). The white solid obtain was filtered, washed with water and dried.[Yield: 16 g, 90percent]
87.3% With methanesulfonic acid In dichloromethane at 20℃; for 8 h; Example 2; Preparation of 2 -( 1 -adamantyl)-4-bromophenol (III) : A mixture of p-bromophenol (10.0 g, 57.8 mmol and 1-adamantanol (8.78 g, 57.76 mmol) in dichloromethane (50 ml) and methane sulphonic acid (3.74 ml, 57.8 mmol) was stirred for 8 h at room temperature . The reaction mixture was diluted with water and dichloromethane was distilled. The white solid obtained was filtered, washed with water and dried.[Yield: 15.5 g, 87.3 percent]
86% With sulfuric acid In dichloromethane (a)
2-(1-adamantyl)-4-bromophenol.
34.6 g (200 mmol) of p-bromophenol and 30.4 g (200 mmol) of 1-adamantanol are dissolved in 100 ml of dichloromethane.
To the resulting solution there are slowly added 10 ml of concentrated sulfuric acid.
The mixture is stirred for 8 hours at ambient temperature, poured into water, neutralized with sodium bicarbonate, extracted with methylene chloride, dried and evaporated.
After recrystallization in isooctane 52.8 g of the expected product are obtained. Yield--86percent.
Melting point: 140°-141° C.
86% With sulfuric acid In dichloromethane (a') 2-(1-adamantyl)-4-bromophenol
34.6 g (200 mmol) of p-bromophenol and 30.4 g (200 mmol) of 1-adamantanol are dissolved in 100 ml of dichloromethane.
There are slowly added 10 ml of concentrated sulfuric acid and the reaction mixture is stirred for 8 hours at ambient temperature.
The reaction mixture is then poured into water, neutralized with sodium bicarbonate, extracted with methylene chloride, dried and evaporated.
After recrystallization in isooctane 52.8 g of the desired product are obtained.
Yield: 86percent.
Melting point: 140°-141° C.
75% With sulfuric acid In dichloromethane at 0℃; for 1 h; 100 mL three-neck eggplant flask fully dried (dropping funnel, three-way cock, 4-bromophenol (manufactured by Tokyo Chemical Industry Co., Ltd.) was added to a magnetic stirring bar) (20 mmol) of 1-adamantanol and 30 mL of dichloromethane, and the mixture was cooled to 0 ° C. in an ice bath, 1.07 mL (20 mmol) of sulfuric acid was added dropwise, and the mixture was allowed to react for 1 hour as it was. The reaction solution was neutralized with a saturated aqueous sodium hydrogencarbonate solution (100 mL) After extraction with 50 mL × 2 of dichloromethane, the organic phase was washed twice with 50 mL of pure water, Drying over MgSO 4 and distilling off the solvent under reduced pressure gave a crude product . The crude product was reprecipitated with hexane to give compound 15 as a mixture of 4.61 (75percent, white solid)
63%
Stage #1: With sulfuric acid In dichloromethane at 20℃; for 48 h;
2. Preparation of 2-Adamantan-1-yl-4-bromophenol; 51.9 g (300 mmol) of 4-bromophenol and 45.7 g (300 mmol) of adamantan-1-ol are dissolved in 150 ml of dichloromethane; 15 ml of 98percent sulfuric acid are slowly run in and the reaction medium is stirred at ambient temperature for two days. The medium is evaporated to dryness, taken up with water, neutralized to pH=7-8, filtered, taken up in THF, dried over MgSO4, evaporated, and purified on a silica column, elution being carried out with a 10/90 ether/heptane mixture. A thick oil is obtained (m=58 g, yield=63percent).
74% With sulfuric acid In dichloromethane d.
2-(1-Adamantyl)-4-bromophenol
To a mixture of 4-bromophenol (34.60 g, 200 mmol) and 1-adamantanol (30.45 g, 200 mmol) in 100 mL of anhydrous CH2Cl2 at room temperature was added dropwise over 10-15 minutes concentrated H2SO4 (11 mL).
After 1.5 hours a thick suspension resulted and the reaction was allowed to continue for a total of 24 hours.
The suspension was carefully poured into ice water and neutralized with solid NaHCO3.
The resulting layers were separated and the aqueous layer extracted with CH2Cl2 (2*).
The combined organics were washed with brine, dried (MgSO4) and filtered.
The solvent was removed under reduced pressure and the resulting solid was purified on silica gel (hexane:ethyl acetate 85:15), the impure fractions were further purified by recrystallization from hexane and the two lots combined to give 45.2 g (74percent) of 2-(1-adamantyl)-4-bromophenol. 1H NMR (300 MHz; CDCl3): δ1.77 (s, 6 H), 2.08 (s, 9 H), 4.81 (s, 1 H), 6.53 (d, J=8.4 Hz, 1 H), 7.14 (dd, J1=8.7 Hz, J2=2.4 Hz, 1 H), 7.29 (d, J=2.4 Hz, 1 H).
77% With sulfuric acid In dichloromethane e.
2-Adamantan-1-yl-4-bromophenol
A 2.0 L three-neck flask attached with a power-stirrer was charged with 4-bromophenol (340.8 g, 1.97 mmol) and 1-adamantanol (300.0 g, 1.97 mmol) in 1.0 L of anhydrous CH2Cl2 at room temperature.
Stirring was initiated and once all the reagents were solubilized then concentrated H2SO4 (105 mL, 193.2 g, 1.97 mmol, 1.0 eq) was added dropwise over 15-30 minutes.
After approximately 1.0 hour a suspension resulted and the reaction was allowed to continue for a total of 24 hours.
The suspension was carefully poured into ice water and neutralized with solid NaHCO3.
The resulting layers were separated and the aqueous layer extracted with CH2Cl2 (2*).
The combined organics were washed with brine, dried (MgSO4) and filtered.
The solvent was removed under reduced pressure and the resulting solid was suspended in a minimal amount of hexanes.
After stirring at room temperature for an hour the solid was collected via filtration and dried under reduced pressure to give 495.0 g (77percent) of 2-adamantan-1-yl-4-bromophenol as a white solid. 1H NMR (300 MHz; CDCl3): δ1.77 (s, 6 H), 2.08 (s, 9 H), 4.81 (s, 1 H), 6.53 (d, J=8.4 Hz, 1 H), 7.14 (dd, J1=8.7 Hz, J2=2.4 Hz, 1 H), 7.29 (d, J=2.4 Hz, 1 H).

Reference: [1] Bioorganic Chemistry, 2011, vol. 39, # 4, p. 151 - 158
[2] RSC Advances, 2016, vol. 6, # 73, p. 68560 - 68567
[3] Organic Process Research and Development, 2006, vol. 10, # 2, p. 285 - 288
[4] Beilstein Journal of Organic Chemistry, 2012, vol. 8, p. 227 - 233
[5] Patent: WO2007/125542, 2007, A2, . Location in patent: Page/Page column 13-14
[6] Patent: WO2007/125542, 2007, A2, . Location in patent: Page/Page column 14
[7] Patent: WO2007/125542, 2007, A2, . Location in patent: Page/Page column 14
[8] Journal of Medicinal Chemistry, 1995, vol. 38, # 26, p. 4993 - 5006
[9] Patent: US4717720, 1988, A,
[10] Patent: US4740519, 1988, A,
[11] Patent: JP5769443, 2015, B2, . Location in patent: Paragraph 0187
[12] Patent: US2007/4698, 2007, A1, . Location in patent: Page/Page column 4
[13] Patent: WO2010/43000, 2010, A1, . Location in patent: Page/Page column 80
[14] Journal of Medicinal Chemistry, 2007, vol. 50, # 11, p. 2622 - 2639
[15] Patent: US2003/92758, 2003, A1,
[16] Patent: US2002/143182, 2002, A1,
[17] Patent: US2002/143182, 2002, A1,
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YieldReaction ConditionsOperation in experiment
75% With sulfuric acid In dichloromethane at 20℃; for 20 h; 1-(5-Bromo-2-methoxyphenyl)-adamantane [0145] [0146] Reagent grade concentrated H2S04 (11 mL) was added dropwise to a solution of 1- adamantol (30.25 g, 200 mmol) and 4-bromoanisole (37.21g, 200 mmol) in 130 mL of CH2Cl2. The light pink solution was stirred at ambient temperature for 20 hours. The solvent was decanted, water (100 mL) and hexane (100 mL) were added and the solid was filtered and washed with hexane and dried to give 31 g of the product as a white powder. The supernatant was diluted with hexane, washed with water and brine, dried over MgS04 and filtered thru a silica gel pad. The solvent was removed and the solid was recrystallized from hexane to yield 17 g of the product as a white powder. [0147] Yield: 65 g (75percent) ; white solid; Rf= 0.9 in 25percent EtOAc-hexane. 1H NMR (CDC13, 300 MHz) No. 1.78 (s, 6H), 2.08 (s, 9H), 3.81 (s, 3H), 6.72 (d, 1H), 7.24 (dd, 1H), 7.28 (m, 1H)
75% With sulfuric acid In dichloromethane at 20℃; for 20 h; Reagent grade concentrated H2SO4 (11 mL) was added dropwise to a solution of 1- adamantol (30.25 g, 200 mmol) and 4-bromoanisole (37.21g, 200 mmol) in 130 mL of CH2Cl2. The light pink solution was stirred at ambient temperature for 20 hours. The solvent was decanted, water (100 mL) and hexane (100 mL) were added and the solid was filtered and washed with hexane and dried to give 31 g of the product as a white powder. The supernatant was diluted with hexane, washed with water and brine, dried over MgSO4 and filtered thru a silica gel pad. The solvent was removed and the solid was recrystallized from hexane to yield 17 g of the product as a white powder.[0157] Yield: 48 g (75percent); white solid; Rf= 0.9 in 25percent EtOAc-hexane. IH NMR (CDC13, 300 MHz) D 1.78 (s, 6H)3 2.08 (s, 9H), 3.81 (s, 3H), 6.72 (d, IH)5 7.24 (dd, IH)5 7.28 (m, IH).
72% With sulfuric acid In dichloromethane for 5 h; Step A. 2-(1-adamantyl)-4-bromoanisoleExample 1; In a 1 L flask equipped with a stirrer, a reflux condenser and a dropping funnel, a mixture of 50 g (0.33 M) 1-adamantanol, 68 g (45.5 mL, 0.36 M) 4-bromoanisole and 500 mL of methylene chloride is prepared. The mixture is stirred until dissolved and then 35 g (19 mL, 0.36 M) sulfuric acid added during one hour. The reaction mixture is stirred for 4 hours, 200 mL of water added, stirred for another 10 min, transferred to separating funnel and the organic layer collected, which is neutralized by two portions of 100 mL 10percent sodium carbonate solution. Methylene chloride is distilled off completely, the residue dissolved in 300 mL of ethyl acetate, filtered, concentrated to 200 mL and left to crystallize at 0° C. for 16 h. The crystals are filtered off, washed by 50 mL of cold ethyl acetate and dried at 100° C. for one hour. 2-adamantyl-4-bromoanisole, 76 g (72percent) with m.p. 140-141° C. is obtained.NMR (500 MHz, DMSO D6) δ: 1.75 (s, 6H), 2.03 (s, 9H), 3.81 (s, 3H), 6.82 (d, 1H, J=8 Hz), 7.17 (s, 1H), 7.23 (d, 1H, J=8 Hz).Scaling the synthesis up 10 times did not change either the yield or quality of the 2-(1-adamantyl)-4-bromoanisole.
72% With sulfuric acid In dichloromethane for 5 h; Step A. 2-(1-adamantyl)-4-bromoanisole; EXAMPLE 1In a 1 L flask equipped with a stirrer, a reflux condenser and a dropping funnel, a mixture of 50 g (0.33 M) 1-adamantanol, 68 g (45.5 mL, 0.36 M) 4-bromoanisole and 500 mL of methylene chloride is prepared. The mixture is stirred until dissolved and then 35 g (19 mL, 0.36 M) of sulfuric acid added during one hour. The reaction mixture is stirred for 4 hours, 200 mL of water added, stirred for another 10 min, transferred to a separating funnel and the organic layer collected. It is neutralized by two portions of 100 mL 10percent sodium carbonate solution. Methylene chloride is distilled off completely, the residue dissolved in 300 mL of ethyl acetate, filtered, concentrated to 200 mL and left to crystallize at about 0° C. for 16 h. The crystals are filtered off, washed by 50 mL of cold ethyl acetate and dried at 100° C. for one hour. 2-adamantyl-4-bromoanisole, 76 g (72percent) with m.p. 140-141° C. is obtained.NMR (500 MHz, DMSO D6)δ: 1.75 (s, 6H), 2.03 (s, 9H), 3.81 (s, 3H), 6.82 (d, 1H, J=8 Hz), 7.17 (s, 1H), 7.23 (d, 1H, J=8 Hz).Scaling the synthesis up 10 times did not change either the yield or quality of the 2-(1-adamantyl)-4-bromoanisole

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[2] Patent: WO2005/108338, 2005, A1, . Location in patent: Page/Page column 47
[3] Patent: WO2007/28104, 2007, A2, . Location in patent: Page/Page column 50-51
[4] Patent: US2010/76219, 2010, A1, . Location in patent: Page/Page column 2
[5] Patent: US2010/160677, 2010, A1, . Location in patent: Page/Page column 3
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[2] Journal of Medicinal Chemistry, 2003, vol. 46, # 6, p. 909 - 912
[3] European Journal of Medicinal Chemistry, 2014, vol. 79, p. 251 - 259
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