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Product Details of [ 15852-73-0 ]

CAS No. :15852-73-0 MDL No. :MFCD00004629
Formula : C7H7BrO Boiling Point : -
Linear Structure Formula :- InChI Key :FSWNRRSWFBXQCL-UHFFFAOYSA-N
M.W :187.03 Pubchem ID :85141
Synonyms :

Calculated chemistry of [ 15852-73-0 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.27
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) : -9.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.04
Log Po/w (XLOGP3) : -3.52
Log Po/w (WLOGP) : 1.79
Log Po/w (MLOGP) : 2.3
Log Po/w (SILICOS-IT) : 2.37
Consensus Log Po/w : 1.0

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 3.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.79
Solubility : 1150.0 mg/ml ; 6.18 mol/l
Class : Highly soluble
Log S (Ali) : 3.68
Solubility : 888000.0 mg/ml ; 4750.0 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -3.08
Solubility : 0.156 mg/ml ; 0.000832 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.11

Safety of [ 15852-73-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 15852-73-0 ]

* 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 [ 15852-73-0 ]
  • Downstream synthetic route of [ 15852-73-0 ]

[ 15852-73-0 ] Synthesis Path-Upstream   1~34

  • 1
  • [ 15852-73-0 ]
  • [ 108-95-2 ]
  • [ 13826-35-2 ]
YieldReaction ConditionsOperation in experiment
84% With sodium dodecyl-sulfate; potassium carbonate In water at 80℃; for 10 h; Green chemistry General procedure: To a stirred suspension of appropriate aryl halide(2.0 mmol) and phenol (2.0 mmol) in 6 ml water, Ni-alumina (0.125g, 6 mol percent ofnickel metal) was added followed by K2CO3 (0.28 g, 2mmol) and SDS (0.04 g, 8 molpercent). The reaction mixture was stirred for therequired period of time at 80°C till the reaction was complete (monitored withTLC). Then the reaction mixture was cooled to room temperature, ethyl acetate(20 mL) was added to dissolve the product and the catalyst was separated simplyby filtration. The residue (recovered catalyst) was thoroughly washed withEtOAc (4×5 mL) followed by water (2×10 mL). The aqueous reaction mixture was repeatedly extracted with ethyl acetate (3×5 mL). The combined organic extractswere washed with water (3× 10 mL) and dried over anhydrous Na2SO4.The crude product was obtained by removal of the solvent under reduced pressure which was furtherpurified by filtration chromatography on a short column of silica gel using1-4percent ethyl acetate-hexane as eluent.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 51, p. 7082 - 7088
  • 2
  • [ 15852-73-0 ]
  • [ 932-77-4 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 10, p. 3061 - 3064
[2] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 11, p. 3434 - 3436
[3] Journal of the American Chemical Society, 2000, vol. 122, # 46, p. 11315 - 11319
[4] Russian Journal of Organic Chemistry, 2002, vol. 38, # 12, p. 1769 - 1774
[5] Journal fuer Praktische Chemie (Leipzig), 1921, vol. <2> 101, p. 333
[6] Journal of the American Chemical Society, 1951, vol. 73, p. 2813,2818
[7] Journal of the Chemical Society, 1935, p. 1815,1818
  • 3
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  • [ 823-78-9 ]
  • [ 932-77-4 ]
Reference: [1] Synthesis, 2008, # 24, p. 3937 - 3940
  • 4
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  • [ 25724-79-2 ]
Reference: [1] Russian Journal of Organic Chemistry, 2002, vol. 38, # 12, p. 1769 - 1774
  • 5
  • [ 15852-73-0 ]
  • [ 22726-00-7 ]
  • [ 105946-57-4 ]
Reference: [1] Advanced Synthesis and Catalysis, 2010, vol. 352, # 14-15, p. 2588 - 2598
  • 6
  • [ 15852-73-0 ]
  • [ 823-78-9 ]
Reference: [1] Organic Process Research and Development, 2002, vol. 6, # 2, p. 190 - 191
[2] Organic Letters, 2018, vol. 20, # 10, p. 3061 - 3064
[3] Organic Letters, 2008, vol. 10, # 11, p. 2143 - 2145
[4] Journal of the American Chemical Society, 2015, vol. 137, # 30, p. 9567 - 9570
  • 7
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  • [ 823-78-9 ]
  • [ 932-77-4 ]
Reference: [1] Synthesis, 2008, # 24, p. 3937 - 3940
  • 8
  • [ 3132-99-8 ]
  • [ 15852-73-0 ]
YieldReaction ConditionsOperation in experiment
99.8% With sodium tetrahydroborate In ethanol at 20 - 25℃; Example 49
(3-Bromophenyl)methanol
Sodium borohydride (7.1 g, 186.1 mmol) in several portions was added to a solution of 3-bromobenzaldehyde (114.8 g, 620.4 mmol) in EtOH (650 mL) at 25° C.
Then the mixture was stirred for 1 h at room temperature.
The reaction was quenched with water (200 mL).
After removing EtOH, the residue was dissolved in AcOEt (500 mL), and filtered.
The filtrate was washed with water (150 mL), brine (150 mL), and dried over Na2SO4.
After removing the solvent, 115.8 g of the title compound was obtained (yield: 99.8percent).
99.8% at 20 - 25℃; Example 49
(3-Bromophenyl)methanol
Sodium borohydride (7.1 g, 186.1 mmol) in several portions was added to a solution of 3-bromobenzaldehyde (114.8 g, 620.4 mmol) in EtOH (650 mL) at 25° C.
Then the mixture was stirred for 1 h at room temperature.
The reaction was quenched with water (200 mL).
After removing EtOH, the residue was dissolved in AcOEt (500 mL), and filtered.
The filtrate was washed with water (150 mL), brine (150 mL), and dried over Na2SO4.
After removing the solvent, 115.8 g of the title compound was obtained (yield: 99.8percent).
99.8%
Stage #1: With sodium tetrahydroborate In ethanol at 20 - 25℃;
Stage #2: With water In ethanol
Example 52
(3-Bromophenyl)methanol
To a solution of 3-bromobenzaldehyde (114.8 g, 620.4 mmol) in EtOH (650 mL), NaBH4 (7.1 g, 186.1 mmol) was added in several portions at 25° C.
Then the mixture was stirred for 1 h at room temperature.
The reaction was quenched with water (200 mL).
After removing EtOH, the residue was dissolved in AcOEt (500 mL), and filtered.
The filter was washed with water (150 mL), brine (150 mL), and dried over Na2SO4.
After removing the solvent, 115.8 g of the title compound was obtained (Yield: 99.8percent).
99.8% at 20 - 25℃; for 1 h; Example 49 (3-Bromophenyl)methanolSodium borohydride (7.1 g, 186.1 mmol) in several portions was added to a solution of 3- bromobenzaldehyde (114.8 g, 620.4 mmol) in EtOH (650 mL) at 25 0C. Then the mixture was stirred for 1 h at room temperature. The reaction was quenched with water (200 mL). After removing EtOH, the residue was dissolved in AcOEt (500 mL), and filtered. The filtrate was washed with water (150 mL), brine (150 mL), and dried over Na2SOφ After removing the solvent, 115.8 g of the title compound was obtained (yield: 99.8percent).
99% With sodium tetrahydroborate In methanol at 0℃; Inert atmosphere General procedure: Aldehyde (1 mmol) was dissolved in 10 ml ofmethanol(ethanol for ketones) and cooled to 0oC. NaBH4 (3 mmol) was then added inone portion and the reaction was allowed to stir until completion as indicatedby TLC (9:1 heptanes/ethyl acetate). The reaction was quenched with 0.1 N NaOH(10 ml) and extracted three times with ethyl actetate. The organic layer waswashed with brine and dried over Na2SO4. The solvent wasremoved under reduced pressure and the resulting yellow oil was subjected toflash chromatography.
97% With 2BH4(1-)*Zn(2+)*Cl2Na2 In acetonitrile at 20℃; for 0.0333333 h; General procedure: In a round-bottomed flask (10 mL), equipped with a magneticstirrer bar, a solution of acetophenone (0.121 g, l mmol) was prepared in CH3CN(3 mL). To this solution, Zn(BH4)2/2NaCl (0.210 g,1 mmol) was added. The resulting mixture was stirred at room temperature for 60 min. The reaction was monitored by TLC(eluent; Hexane/EtOAc: 10/1). After completion of the reaction, distilled water (5 mL) was added to the reaction mixture and stirred for 5 min. The mixture was extracted with CH2Cl2 (3 ×8 mL) and dried over anhydrous Na2SO4. Evaporation of the solvent followed column chromatography of the resulting crude material over silica gel (eluent; Hexane/EtOAc: 10/1) afforded crystals of 1-phenylethanol (0.l1 g, 93 percent yield,Table 2, entry 11).
95% for 0.00833333 h; Microwave irradiation General procedure: In a round-bottomedflask (10 mL) charged with distilled water (5 mL), LiBH4 (0.022 g, -Immo)andbenzaldehyde (0.106 g, 1 mmol) was added. After fitting the flaskto the external condenser at the inside of the oven, the mixture was irradiatedwith a microwave oven (30percentpower amplitude, 300 W) for30 sec. The progress of the reaction was monitored by TLC(eluent;CCI4/Et20: 5/2). At the end of the reduction, distilled water(5 mL) was added to the reaction mixture and it wasthen extracted with CH2Cl2(2Χ10 mL). The combined extracts were dried over anhydrous sodium sulfate. evaporation of the solvent afforded the pure liquid benzyl alcohol(0.102 g, 95percent).
94% With sodium tetrahydroborate In ethanol at 0℃; for 1 h; Cooling with ice Compound 2 was prepared according to Eur. J. Org. Chem, 2002, 19, 3326-3335. In a 250 mL roundbottom was added 3-bromobenzaldehyde 1 (10.0 g, 54.0 mmol) and EtOH (25 mL). The solution was cooled to 0 °C in an ice-water bath, sodium borohydride (1.1 1 g, 29.5 mmol) was added, and the mixture was stirred at 0 °C for 1 h. Sodium sulfate decahydrate was added, and the reaction was stirred at rt for 1 h to quench the borohydride. Diethyl ether was added, and the mixture was washed with water. The organic layer was dried with sodium sulfate and concentrated under vacuum to give 2 (9.50 g, 94percent) as a clear oil. 1H NMR (400 MHz, CDCI3): 2.34 (br. s, 1 H), 4.61 (br. s, 2 H), 7.13 - 7.33 (m, 2 H), 7.40 (d, J = 7.6 Hz, 1 H), 7.49 (s, 1 H).
94% at 0℃; for 1 h; 2.
F.
Synthesis of X069 Succinate Ester
Compound 2 was prepared according to Eur. J. Org. Chem, 2002, 19, 3326-3335.
In a 250 mL roundbottom was added 3-bromobenzaldehyde 1 (10.0 g, 54.0 mmol) and EtOH (25 mL).
The solution was cooled to 0° C. in an ice-water bath, sodium borohydride (1.11 g, 29.5 mmol) was added, and the mixture was stirred at 0° C. for 1 h.
Sodium sulfate decahydrate was added, and the reaction was stirred at rt for 1 h to quench the borohydride.
Diethyl ether was added, and the mixture was washed with water.
The organic layer was dried with sodium sulfate and concentrated under vacuum to give 2 (9.50 g, 94percent) as a clear oil. 1H NMR (400 MHz, CDCl3): 2.34 (br. s, 1H), 4.61 (br. s, 2H), 7.13-7.33 (m, 2H), 7.40 (d, J=7.6 Hz, 1H), 7.49 (s, 1H).
93% With zinc(II) tetrahydroborate In water for 0.0166667 h; Microwave irradiation; Green chemistry General procedure: Zn(BH4)2was prepared from ZnCl4 (5.452g, 0.04 mol) and NaBH4(3.177 g, 0.084 mol)according to an available procedure in the literature11.In a round-bottomed flask (10 mL) charged withdistilled water (5 mL), Zn(BH4)2(0.095 g, 1mmol)and benzaldehyde (0.106 g, 1 mmol) was added.After fitting the flask to the external condenser atthe inside of the oven, the mixture was irradiatedwitha microwave oven (30percent power amplitude, 300 W)for60 sec. The progress of the reaction wasmonitored by TLC(eluent; CH2Cl2). At the end of thereduction, distilledwater (5 mL) was added to thereaction mixture and it wasthen extracted withCH2Cl2(2×10 mL). The combined extracts were dried over anhydrous sodium sulfate. Evaporationofthe solvent afforded the pure liquid benzyl alcohol(0.102 g, 95percent).
80% With sodium dithionite; sodium hydrogencarbonate In water; isopropyl alcohol at 110℃; for 2.66667 h; Flow reactor General procedure: A 0.165 M stock solution of aldehyde or ketone (1 equiv) was prepared by dissolution in (1:1:2 IPA/H2O/NaHCO3 [1 M]). A 0.75 M stock solution of sodium dithionite (4,5 equiv) was prepared by dissolution in (1:1:2 IPA/H2O/NaHCO3 [1 M]). The injection loops (10 mL) unless otherwise stated were primed with the two stock solutions respectively. The solutions were then pumped continuously through a 2 mL mixing chip at ambient temperature followed by a 14 mL HT Teflon coil at 110 °C (aldehydes and ketones). Unless otherwise stated the flow rate was set to 0.25 mL·min−1 (64 min residence) for aldehydes and 0.20 mL·min−1 (80 min residence) for ketones. Product work-up and isolation was achieved using the approach described for the batch reductions.

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YieldReaction ConditionsOperation in experiment
98% With hydrogenchloride In tetrahydrofuran; hexane Part A
3-Bromobenzyl alcohol (2.0 g, 10.7 mmol) was dissolved in dry THF (50 ml) in a dry 100 ml flask flushed with nitrogen.
The mixture was chilled in a dry ice/acetone bath. n-Butyl lithium (11 ml of a 2.13M solution in hexane, 23.5 mmol) was added.
The reaction was warmed to room temperature for 1 hour, then cooled in an ice water bath.
Trimethyl borate (1.3 ml, 11.2 mmol) was added and the mixture was stirred at room temperature overnight, then treated with 2N aqueous HCl to pH 2, and stirred for 3 hours.
Brine (15 ml) was added, and the mixture was extracted with ethyl acetate (3*15 ml).
The organic materials were combined, dried (MgSO4) then concentrated under reduced pressure which gave of 3-hydroxymethylbenzeneboronic acid (98percent) as a clear oil.
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  • [ 15852-73-0 ]
  • [ 123987-13-3 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.5 h;
Stage #2: With chloro-(2-dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) methyl-tert-butyl ether adduct; ruphos In tetrahydrofuran at 75℃; for 1 h; Inert atmosphere
To a solution of (3-bromophenyl)methanol (570 mg, 3.05 mmol) in THF (5 mL) was added LHMDS (7.43 mL, 7.43 mmol) and the mixture was stirred at RT for 30 minutes. Ru-phos precatalyst (97 mg, 0.133 mmol), dicyclohexyl(2',6'-diisopropoxy-[l,l'- biphenyl]-2-yl)phosphine (61.9 mg, 0.133 mmol), and 1-methylpiperazine (0.441 mL, 3.98 mmol) were added, the mixture was degassed with a stream of nitrogen and heated to 75 °C for 1 h. The mixture was then diluted with DCM and washed with water. The organic layer was concentrated under reduced pressure and the residue was purified by Si02gel chromatography (0-20percent MeOH in DCM) to give the title compound (506 mg, 80percent). MS(ES+) C12H18N20 requires: 206, found: 207 [M+H]+.
Reference: [1] Patent: WO2014/31928, 2014, A2, . Location in patent: Paragraph 0472
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