[ CAS No. 18385-87-0 ] {[proInfo.proName]}

Name: 18385-87-0|6-Bromo-2H-chromene|95%
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SKU: A842793
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Quality Control of [ 18385-87-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 18385-87-0 ]

CAS No. :	18385-87-0	MDL No. :	MFCD10688514
Formula :	C₉H₇BrO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YTNWANXDKHOVBF-UHFFFAOYSA-N
M.W :	211.06	Pubchem ID :	10242241
Synonyms :

Calculated chemistry of [ 18385-87-0 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.11
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	48.61
TPSA :	9.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.49 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.43
Log Po/w (XLOGP3) :	2.95
Log Po/w (WLOGP) :	2.75
Log Po/w (MLOGP) :	2.69
Log Po/w (SILICOS-IT) :	3.04
Consensus Log Po/w :	2.77

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.41
Solubility :	0.082 mg/ml ; 0.000388 mol/l
Class :	Soluble
Log S (Ali) :	-2.81
Solubility :	0.33 mg/ml ; 0.00156 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.36
Solubility :	0.0926 mg/ml ; 0.000439 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.6

Safety of [ 18385-87-0 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 18385-87-0 ]

* 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 [ 18385-87-0 ]
Downstream synthetic route of [ 18385-87-0 ]

[ 18385-87-0 ] Synthesis Path-Upstream 1~1

1
[ 18385-87-0 ]
[ 1373215-15-6 ]

Reference： [1] Patent: US2012/95020, 2012, A1,
[2] Patent: US2012/95020, 2012, A1,
[3] Patent: US2012/95020, 2012, A1,
[4] Patent: US2012/95020, 2012, A1,

[ 18385-87-0 ] Synthesis Path-Downstream 1~45

1
E-phenyl<3-(p-bromophenoxy)-1-propenyl>iodonium tetrafluoroborate [ No CAS ]
[ 18385-87-0 ]

Yield	Reaction Conditions	Operation in experiment
71%	In d⁽⁴⁾-methanol at 60℃; for 0.5h;

Reference： [1]Ochiai, Masahito; Takaoka, Yoshikazu; Sumi, Kenzo; Nagao, Yoshimitsu [Journal of the Chemical Society. Chemical communications, 1986, # 17, p. 1382 - 1384]

2
[ 23250-03-5 ]
[ 1761-61-1 ]
[ 18385-87-0 ]

Yield	Reaction Conditions	Operation in experiment
35%	With potassium carbonate In chlorobenzene at 120℃; for 20h;

Reference： [1]Billeret; Blondeau; Sliwa [Synthesis, 1993, # 9, p. 881 - 884]

3
[ 18385-87-0 ]
trans-3,6-dibromo-3,4-dihydro-2H-1-benzopyran-4-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With N-Bromosuccinimide; water In dimethyl sulfoxide at 0 - 5℃; for 1.5h;	38 Heat a solution of 6-bromochroman-4-ol (25.0 g, 109.1 mmol) in toluene (500 mL) to 100° C. Add p-toluenesulfonic acid monohydrate (1.1 g, 5.5 mmol) and, using a Dean-Stark trap to collect water, stir at 100° C. for 2 hr. Remove the heat source and quench the reaction mixture with ice cold 0.5N NaOH (250 mL). Further cool the reaction mixture to 5-10° C., and then separate the layers. Wash the organic layer with water (25 mL) and concentrate the organics under reduced pressure to approximately half their original volume. Add DMSO (100 mL) and continue to concentrate under reduced pressure until no more toluene distills.Cool the DMSO solution of the intermediate olefin to 0-5° C., add water (17 mL) and re-cool to 0-5° C. Add N-bromosuccinimide (21.7 g, 120.0 mmol) in 5 portions over 30 minutes. Stir at 0-5° C. for 1 hr. Dilute the reaction mixture with ethyl acetate (100 mL) and water (50 mL), stir 10 min., and separate the layers. Back extract the aqueous layer with ethyl acetate (100 mL). Wash the combined organics with 1:1 brine/water (2x50 mL), dry over sodium sulfate and concentrate under reduced pressure to obtain the title compound as a white solid (33.0 g, 99%). 1H NMR (DMSO-d6) δ 4.26 (m, 1H), 4.37 (m, 2H), 4.65 (m, 1H), 6.27 (d, 1H), 6.80 (d, 1H), 7.35 (dd, 1H), 7.46 (bd, 1H). GC/MS m/z (79Br/81Br) 308/310 [M+].
81%	With N-Bromosuccinimide In water; dimethyl sulfoxide at 0℃; for 1h;

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US2012/95020, 2012, A1 Location in patent: Page/Page column 14; 15
[2]Atwal, Karnail S.; Grover, Gary J.; Ferrara, Francis N.; Ahmed, Syed Z.; Sleph, Paul G.; et al. [Journal of Medicinal Chemistry, 1995, vol. 38, # 11, p. 1966 - 1973]

4
[ 33133-45-8 ]
[ 624-65-7 ]
[ 18385-87-0 ]

Yield	Reaction Conditions	Operation in experiment
56.3%	With N,N-diethylaniline for 12h; Heating;

Reference： [1]Atwal, Karnail S.; Grover, Gary J.; Ferrara, Francis N.; Ahmed, Syed Z.; Sleph, Paul G.; et al. [Journal of Medicinal Chemistry, 1995, vol. 38, # 11, p. 1966 - 1973]

5
1-Allyloxy-4-bromo-2-vinyl-benzene [ No CAS ]
[ 18385-87-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With Grubbs catalyst first generation In dichloromethane for 2h; Ambient temperature;
94%	In dichloromethane at 20℃; for 2h;
93%	In toluene at 80℃; for 4h;

93 % Chromat.	In dichloromethane at 40℃; for 3h;
94 % Chromat.	In dichloromethane at 20℃; for 3h;

Reference： [1]Chang, Sukbok; Grubbs, Robert H. [Journal of Organic Chemistry, 1998, vol. 63, # 3, p. 864 - 866]
[2]Fuerstner, Alois; Guth, Oliver; Dueffels, Arno; Seidel, Guenter; Liebl, Monika; Gabor, Barbara; Mynott, Richard [Chemistry - A European Journal, 2001, vol. 7, # 22, p. 4811 - 4820]
[3]Fuerstner, Alois; Liebl, Monika; Lehmann, Christian W.; Picquet, Michel; Kunz, Rainer; Bruneau, Christian; Touchard, Daniel; Dixneuf, Pierre H. [Chemistry - A European Journal, 2000, vol. 6, # 10, p. 1847 - 1857]
[4]Ackermann, Lutz; Fuerstner, Alois; Weskamp, Thomas; Kohl, Florian J.; Herrmann, Wolfgang A. [Tetrahedron Letters, 1999, vol. 40, # 26, p. 4787 - 4790]
[5]Fuerstner, Alois; Hill, Anthony F.; Liebl, Monika; Wilton-Ely, James D. E. T. [Chemical Communications, 1999, # 7, p. 601 - 602]

Yield	Reaction Conditions	Operation in experiment
	With ethanol; sodium ethanolate Erhitzen des Reaktionsprodukts;

7
[ 40359-62-4 ]
[ 18385-87-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) NaH / 1.) THF, room temp., 2.) THF, room temp. 2: 99 percent / 2(PCy₃)2Ru=CHPh> / CH₂Cl₂ / 2 h / Ambient temperature

Reference： [1]Chang, Sukbok; Grubbs, Robert H. [Journal of Organic Chemistry, 1998, vol. 63, # 3, p. 864 - 866]

8
[ 1761-61-1 ]
[ 18385-87-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: K₂CO₃ / acetone 2: 1.) NaH / 1.) THF, room temp., 2.) THF, room temp. 3: 99 percent / 2(PCy₃)2Ru=CHPh> / CH₂Cl₂ / 2 h / Ambient temperature
	Multi-step reaction with 2 steps 1: tetrahydrofuran / 0.5 h / -78 - 20 °C / Inert atmosphere 2: [2,2]bipyridinyl; iron(III) chloride / tetrahydrofuran / 5 h / 20 - 80 °C / Microwave irradiation; Inert atmosphere

Reference： [1]Chang, Sukbok; Grubbs, Robert H. [Journal of Organic Chemistry, 1998, vol. 63, # 3, p. 864 - 866]
[2]Calmus; Corbu; Cossy [Advanced Synthesis and Catalysis, 2015, vol. 357, # 7, p. 1381 - 1386]

9
[ 18385-87-0 ]
trans-4-amino-3,4-dihydro-3-hydroxy-2H-1-benzopyran-6-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 81 percent / NBS / dimethylsulfoxide; H₂O / 1 h / 0 °C 2: 97 percent / 30percent aq. NH₄OH / tetrahydrofuran; ethanol / 48 h 3: 87.3 percent / 20percent aq. Na₂CO₃ / tetrahydrofuran / Ambient temperature 4: 58 percent / N-methylpyrrolidone / 3 h / 200 °C 5: 72 percent / 2.5 N aq. H₂SO₄ / dioxane / 60 h / 75 °C

Reference： [1]Atwal, Karnail S.; Grover, Gary J.; Ferrara, Francis N.; Ahmed, Syed Z.; Sleph, Paul G.; et al. [Journal of Medicinal Chemistry, 1995, vol. 38, # 11, p. 1966 - 1973]

10
[ 18385-87-0 ]
trans-N-(6-bromo-3,4-dihydro-3-hydroxy-2H-1-benzopyran-4-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 81 percent / NBS / dimethylsulfoxide; H₂O / 1 h / 0 °C 2: 97 percent / 30percent aq. NH₄OH / tetrahydrofuran; ethanol / 48 h 3: 87.3 percent / 20percent aq. Na₂CO₃ / tetrahydrofuran / Ambient temperature

Reference： [1]Atwal, Karnail S.; Grover, Gary J.; Ferrara, Francis N.; Ahmed, Syed Z.; Sleph, Paul G.; et al. [Journal of Medicinal Chemistry, 1995, vol. 38, # 11, p. 1966 - 1973]

11
[ 18385-87-0 ]
trans-N-(6-cyano-3,4-dihydro-3-hydroxy-2H-1-benzopyran-4-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 81 percent / NBS / dimethylsulfoxide; H₂O / 1 h / 0 °C 2: 97 percent / 30percent aq. NH₄OH / tetrahydrofuran; ethanol / 48 h 3: 87.3 percent / 20percent aq. Na₂CO₃ / tetrahydrofuran / Ambient temperature 4: 58 percent / N-methylpyrrolidone / 3 h / 200 °C

Reference： [1]Atwal, Karnail S.; Grover, Gary J.; Ferrara, Francis N.; Ahmed, Syed Z.; Sleph, Paul G.; et al. [Journal of Medicinal Chemistry, 1995, vol. 38, # 11, p. 1966 - 1973]

12
[ 18385-87-0 ]
1-((3R,4S)-6-Cyano-3-hydroxy-chroman-4-yl)-3-phenyl-urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 81 percent / NBS / dimethylsulfoxide; H₂O / 1 h / 0 °C 2: 97 percent / 30percent aq. NH₄OH / tetrahydrofuran; ethanol / 48 h 3: 87.3 percent / 20percent aq. Na₂CO₃ / tetrahydrofuran / Ambient temperature 4: 58 percent / N-methylpyrrolidone / 3 h / 200 °C 5: 72 percent / 2.5 N aq. H₂SO₄ / dioxane / 60 h / 75 °C 6: ethanol / 4 h / Heating

Reference： [1]Atwal, Karnail S.; Grover, Gary J.; Ferrara, Francis N.; Ahmed, Syed Z.; Sleph, Paul G.; et al. [Journal of Medicinal Chemistry, 1995, vol. 38, # 11, p. 1966 - 1973]

13
[ 18385-87-0 ]
C₁₈H₁₅N₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 81 percent / NBS / dimethylsulfoxide; H₂O / 1 h / 0 °C 2: 97 percent / 30percent aq. NH₄OH / tetrahydrofuran; ethanol / 48 h 3: 87.3 percent / 20percent aq. Na₂CO₃ / tetrahydrofuran / Ambient temperature 4: 58 percent / N-methylpyrrolidone / 3 h / 200 °C 5: 72 percent / 2.5 N aq. H₂SO₄ / dioxane / 60 h / 75 °C 6: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / 2 h / Ambient temperature

Reference： [1]Atwal, Karnail S.; Grover, Gary J.; Ferrara, Francis N.; Ahmed, Syed Z.; Sleph, Paul G.; et al. [Journal of Medicinal Chemistry, 1995, vol. 38, # 11, p. 1966 - 1973]

14
[ 18385-87-0 ]
trans-4-amino-6-bromo-3,4-dihydro-3-hydroxy-2H-1-benzopyran hydrobromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 81 percent / NBS / dimethylsulfoxide; H₂O / 1 h / 0 °C 2: 97 percent / 30percent aq. NH₄OH / tetrahydrofuran; ethanol / 48 h

Reference： [1]Atwal, Karnail S.; Grover, Gary J.; Ferrara, Francis N.; Ahmed, Syed Z.; Sleph, Paul G.; et al. [Journal of Medicinal Chemistry, 1995, vol. 38, # 11, p. 1966 - 1973]

15
[ 106-41-2 ]
[ 18385-87-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 96 percent / K₂CO₃, KI / acetone / 18 h / Heating 2: 56.3 percent / N,N-diethylaniline / 12 h / Heating

Reference： [1]Atwal, Karnail S.; Grover, Gary J.; Ferrara, Francis N.; Ahmed, Syed Z.; Sleph, Paul G.; et al. [Journal of Medicinal Chemistry, 1995, vol. 38, # 11, p. 1966 - 1973]

Yield	Reaction Conditions	Operation in experiment
93%		17 Example 17 Example 17 6-Bromo-2H-1-benzopyran. A solution of 2-allyloxy-5-bromostyrene (416 mg) in toluene (20 ml) is added dropwise to a solution of the allenylidene complex (p-cymene)RuCl(PCy3)(=C=C=CPh2)+PF6-(54 mg) in toluene (5 ml) over a period of 1.5 h at 80° C. After stirring at that temperature for another 16 h, the solvent is evaporated and the crude product purified by flash chromatography affording the title compound (341 mg, 93%). 1H NMR (200 MHz, CDCl3): d=7.15 (dd, 1H), 7.04 (d, 1H), 6.62 (d, 1H), 6.31 (dt, 1H), 5.77 (dt, 1H), 4.86 (dd, 2H).

17
[ 18385-87-0 ]
C₉H₉BrO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With water; 4-methylmorpholine N-oxide In acetone; <i>tert</i>-butyl alcohol at 20℃;	3 PREPARATIVE EXAMPLE 3; 13C 3D (+/-)-3; 6-bromo-3-chromanone 3B was prepared from 6- bromo-4-chromanone in a 4 step sequence as outlined in Synthesis, 1980, 621: reduction with NaBH4 (1.2 eq, MeOH-DCM, O 0C to RT, 2h), elimination with pTsOH (cat., toluene, reflux, 3h, 90% for 2-steps), osmylation (cat. OsO4, 1 eq. NMO, water-acetone-tBuOH, RT, overnight) and final treatment with pTsOH (cat., toluene, reflux, 15min, 86% for 2-steps).
	With 4-methylmorpholine N-oxide In water; acetone; <i>tert</i>-butyl alcohol at 20℃;	5 The starting material 6-bromochroman-3-one (5A) was prepared from 6- bromochroman-4-one in a manner similar to that described in the literature (Synthesis, 1980, 621): 6-bromochroman-4-one was reduced with NaBH4 (1.2 eq, MeOH-DCM, O 0C to RT, 2h) and then eliminated with pTsOH (cat., toluene, reflux, 3h, 90% for 2- steps). The resulting 6-bromochromene was subjected to osmylation (cat. OsO4, 1 eq. NMO, water-acetone-tBuOH, RT, overnight) and subsequent treatment with pTsOH (cat., toluene, reflux, 15 min, 86% for 2-steps) to provide 6-bromochroman-3-one (5A).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2010/42475, 2010, A1 Location in patent: Page/Page column 60
[2]Current Patent Assignee: MERCK & CO INC - WO2010/42473, 2010, A1 Location in patent: Page/Page column 92

18
[ 18385-77-8 ]
[ 18385-87-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	With toluene-4-sulfonic acid In toluene Reflux;	Compounds 5h-j; General Procedure General procedure: p-TsOH·H2O (0.25 mol) was added to a solution of alcohol 11(0.1 mol) in anhyd toluene (4 L), and the solution was refluxed until the complete conversion of the starting material. Then, the reaction mixture was cooled to r.t., washed with H2O (21 L), 10% aq NaHCO3 (31 L), and H2O (2*1 L), dried (anhyd Na2SO4), and evaporated under reduced pressure.
	In toluene for 3h; Reflux;	3 PREPARATIVE EXAMPLE 3; 13C 3D (+/-)-3; 6-bromo-3-chromanone 3B was prepared from 6- bromo-4-chromanone in a 4 step sequence as outlined in Synthesis, 1980, 621: reduction with NaBH4 (1.2 eq, MeOH-DCM, O 0C to RT, 2h), elimination with pTsOH (cat., toluene, reflux, 3h, 90% for 2-steps), osmylation (cat. OsO4, 1 eq. NMO, water-acetone-tBuOH, RT, overnight) and final treatment with pTsOH (cat., toluene, reflux, 15min, 86% for 2-steps).
	In toluene for 3h; Reflux;	5 The starting material 6-bromochroman-3-one (5A) was prepared from 6- bromochroman-4-one in a manner similar to that described in the literature (Synthesis, 1980, 621): 6-bromochroman-4-one was reduced with NaBH4 (1.2 eq, MeOH-DCM, O 0C to RT, 2h) and then eliminated with pTsOH (cat., toluene, reflux, 3h, 90% for 2- steps). The resulting 6-bromochromene was subjected to osmylation (cat. OsO4, 1 eq. NMO, water-acetone-tBuOH, RT, overnight) and subsequent treatment with pTsOH (cat., toluene, reflux, 15 min, 86% for 2-steps) to provide 6-bromochroman-3-one (5A).

With toluene-4-sulfonic acid In toluene at 50℃; for 3.83333h; Reflux; Industry scale;

5 To a solution of 6-bromochroman-4-ol (3.98 kg, 17.4 mol) in toluene (18 L) add p-toluenesulfonic acid monohydrate (95 g, 499.42 mmol) at room temperature. Attach a Dean-Stark trap and reflux for 3 hr. and 50 min. Allow the mixture to cool to 50° C. in air and pour into saturated aqueous sodium bicarbonate (10 L) and ice (about 3 kg) with stirring. Separate the two layers. Back extract the aqueous layer with methyl tert-butyl ether (4 L). Wash the organic layer with saturated sodium bicarbonate (10 L) and brine (1x10 L), and evaporate the solvent under reduced pressure to obtain the title compound as a brown oil (4.90 kg, >100%, contains toluene). LCMS m/z (79Br) 209 [M+H]+.

Reference： [1]Sokolov, Andriy; Golovach, Sergey; Kozlinsky, Ihor; Dolia, Krystyna; Tolmachev, Andrey A.; Kuchkovska, Yuliya; Grygorenko, Oleksandr O. [Synthesis, 2019, vol. 51, # 4, p. 848 - 858]
[2]Current Patent Assignee: MERCK & CO INC - WO2010/42475, 2010, A1 Location in patent: Page/Page column 60
[3]Current Patent Assignee: MERCK & CO INC - WO2010/42473, 2010, A1 Location in patent: Page/Page column 92
[4]Current Patent Assignee: ELI LILLY & CO - US2012/95020, 2012, A1 Location in patent: Page/Page column 7

19
[ 33133-45-8 ]
[ 18385-87-0 ]
[ 1263863-01-9 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,2-dichloro-ethane at 70℃; for 23h;

Reference： [1]Efe, Christina; Lykakis, Ioannis N.; Stratakis, Manolis [Chemical Communications, 2011, vol. 47, # 2, p. 803 - 805]

20
[ 18385-87-0 ]
[ 70695-78-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide; water / dimethyl sulfoxide / 1.5 h / 0 - 5 °C 2.1: ammonium hydroxide / isopropyl alcohol; water / 15 h / 20 °C 3.1: D-(+)-camphoric acid / acetonitrile; water / 0.17 h / 70 - 75 °C 3.2: 50 °C

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US2012/95020, 2012, A1

21
[ 18385-87-0 ]
[ 70695-78-2 ]
(3S,4R)-4-amino-6-bromochroman-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: N-Bromosuccinimide; water / dimethyl sulfoxide / 1.5 h / 0 - 5 °C 2: ammonium hydroxide / isopropyl alcohol; water / 15 h / 20 °C 3: CHIRALPAK_.(R). AD-H column / dimethyl amine; methanol / Resolution of racemate

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US2012/95020, 2012, A1

22
[ 18385-87-0 ]
[ 1373215-32-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; water / dimethyl sulfoxide / 1.5 h / 0 - 5 °C 2.1: ammonium hydroxide / isopropyl alcohol; water / 15 h / 20 °C 3.1: D-(+)-camphoric acid / acetonitrile; water / 0.17 h / 70 - 75 °C 3.2: 50 °C 4.1: sodium hydrogencarbonate / water; tetrahydrofuran / 2.25 h / 17 °C / Industry scale
	Multi-step reaction with 4 steps 1: N-Bromosuccinimide; water / dimethyl sulfoxide / 1.5 h / 0 - 5 °C 2: ammonium hydroxide / isopropyl alcohol; water / 15 h / 20 °C 3: CHIRALPAK_.(R). AD-H column / dimethyl amine; methanol / Resolution of racemate 4: sodium hydrogencarbonate / water; tetrahydrofuran / 2.25 h / 17 °C / Industry scale

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US2012/95020, 2012, A1
[2]Current Patent Assignee: ELI LILLY & CO - US2012/95020, 2012, A1

23
[ 18385-87-0 ]
[ 1373215-42-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide; water / dimethyl sulfoxide / 1.5 h / 0 - 5 °C 2.1: ammonium hydroxide / isopropyl alcohol; water / 15 h / 20 °C 3.1: D-(+)-camphoric acid / acetonitrile; water / 0.17 h / 70 - 75 °C 3.2: 50 °C 4.1: sodium hydrogencarbonate / water; tetrahydrofuran / 2.25 h / 17 °C / Industry scale 5.1: sodium t-butanolate / bis(η3-allyl-μ-chloropalladium(II)); tri tert-butylphosphoniumtetrafluoroborate / dimethyl sulfoxide / 0.75 h / 93 - 98 °C / Inert atmosphere 5.2: pH 2.3 5.3: 1 h / 40 °C
	Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide; water / dimethyl sulfoxide / 1.5 h / 0 - 5 °C 2.1: ammonium hydroxide / isopropyl alcohol; water / 15 h / 20 °C 3.1: CHIRALPAK_.(R). AD-H column / dimethyl amine; methanol / Resolution of racemate 4.1: sodium hydrogencarbonate / water; tetrahydrofuran / 2.25 h / 17 °C / Industry scale 5.1: sodium t-butanolate / bis(η3-allyl-μ-chloropalladium(II)); tri tert-butylphosphoniumtetrafluoroborate / dimethyl sulfoxide / 0.75 h / 93 - 98 °C / Inert atmosphere 5.2: pH 2.3 5.3: 1 h / 40 °C

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US2012/95020, 2012, A1
[2]Current Patent Assignee: ELI LILLY & CO - US2012/95020, 2012, A1

24
[ 18385-87-0 ]
[ 1373215-45-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide; water / dimethyl sulfoxide / 1.5 h / 0 - 5 °C 2.1: ammonium hydroxide / isopropyl alcohol; water / 15 h / 20 °C 3.1: D-(+)-camphoric acid / acetonitrile; water / 0.17 h / 70 - 75 °C 3.2: 50 °C 4.1: sodium hydrogencarbonate / water; tetrahydrofuran / 2.25 h / 17 °C / Industry scale 5.1: sodium t-butanolate / bis(η3-allyl-μ-chloropalladium(II)); tri tert-butylphosphoniumtetrafluoroborate / dimethyl sulfoxide / 0.75 h / 93 - 98 °C / Inert atmosphere 5.2: pH 2.3 5.3: 1 h / 40 °C 6.1: sodium tris(acetoxy)borohydride / acetonitrile / 5.67 h / 28 °C
	Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide; water / dimethyl sulfoxide / 1.5 h / 0 - 5 °C 2.1: ammonium hydroxide / isopropyl alcohol; water / 15 h / 20 °C 3.1: D-(+)-camphoric acid / acetonitrile; water / 0.17 h / 70 - 75 °C 3.2: 50 °C 4.1: sodium hydrogencarbonate / water; tetrahydrofuran / 2.25 h / 17 °C / Industry scale 5.1: sodium t-butanolate / bis(η3-allyl-μ-chloropalladium(II)); tri tert-butylphosphoniumtetrafluoroborate / toluene; dimethyl sulfoxide / 4 h / 70 °C / Inert atmosphere 5.2: 0.5 h / pH 6 - 7 5.3: pH 11 - 12 6.1: acetic acid / tetrahydrofuran / 1 h / 35 - 40 °C 6.2: 4 h / 35 - 40 °C
	Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide; water / dimethyl sulfoxide / 1.5 h / 0 - 5 °C 2.1: ammonium hydroxide / isopropyl alcohol; water / 15 h / 20 °C 3.1: CHIRALPAK_.(R). AD-H column / dimethyl amine; methanol / Resolution of racemate 4.1: sodium hydrogencarbonate / water; tetrahydrofuran / 2.25 h / 17 °C / Industry scale 5.1: sodium t-butanolate / bis(η3-allyl-μ-chloropalladium(II)); tri tert-butylphosphoniumtetrafluoroborate / dimethyl sulfoxide / 0.75 h / 93 - 98 °C / Inert atmosphere 5.2: pH 2.3 5.3: 1 h / 40 °C 6.1: sodium tris(acetoxy)borohydride / acetonitrile / 5.67 h / 28 °C

Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide; water / dimethyl sulfoxide / 1.5 h / 0 - 5 °C 2.1: ammonium hydroxide / isopropyl alcohol; water / 15 h / 20 °C 3.1: CHIRALPAK_.(R). AD-H column / dimethyl amine; methanol / Resolution of racemate 4.1: sodium hydrogencarbonate / water; tetrahydrofuran / 2.25 h / 17 °C / Industry scale 5.1: sodium t-butanolate / bis(η3-allyl-μ-chloropalladium(II)); tri tert-butylphosphoniumtetrafluoroborate / toluene; dimethyl sulfoxide / 4 h / 70 °C / Inert atmosphere 5.2: 0.5 h / pH 6 - 7 5.3: pH 11 - 12 6.1: acetic acid / tetrahydrofuran / 1 h / 35 - 40 °C 6.2: 4 h / 35 - 40 °C

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US2012/95020, 2012, A1
[2]Current Patent Assignee: ELI LILLY & CO - US2012/95020, 2012, A1
[3]Current Patent Assignee: ELI LILLY & CO - US2012/95020, 2012, A1
[4]Current Patent Assignee: ELI LILLY & CO - US2012/95020, 2012, A1

25
[ 18385-87-0 ]
[ 1373215-50-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide; water / dimethyl sulfoxide / 1.5 h / 0 - 5 °C 2.1: ammonium hydroxide / isopropyl alcohol; water / 15 h / 20 °C 3.1: D-(+)-camphoric acid / acetonitrile; water / 0.17 h / 70 - 75 °C 3.2: 50 °C 4.1: sodium hydrogencarbonate / water; tetrahydrofuran / 2.25 h / 17 °C / Industry scale 5.1: sodium t-butanolate / bis(η3-allyl-μ-chloropalladium(II)); tri tert-butylphosphoniumtetrafluoroborate / toluene; dimethyl sulfoxide / 4 h / 70 °C / Inert atmosphere 5.2: 0.5 h / pH 6 - 7 5.3: pH 11 - 12
	Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide; water / dimethyl sulfoxide / 1.5 h / 0 - 5 °C 2.1: ammonium hydroxide / isopropyl alcohol; water / 15 h / 20 °C 3.1: CHIRALPAK_.(R). AD-H column / dimethyl amine; methanol / Resolution of racemate 4.1: sodium hydrogencarbonate / water; tetrahydrofuran / 2.25 h / 17 °C / Industry scale 5.1: sodium t-butanolate / bis(η3-allyl-μ-chloropalladium(II)); tri tert-butylphosphoniumtetrafluoroborate / toluene; dimethyl sulfoxide / 4 h / 70 °C / Inert atmosphere 5.2: 0.5 h / pH 6 - 7 5.3: pH 11 - 12

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US2012/95020, 2012, A1
[2]Current Patent Assignee: ELI LILLY & CO - US2012/95020, 2012, A1

26
[ 18385-87-0 ]
(+/-)-trans-4-amino-6-bromochroman-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-Bromosuccinimide; water / dimethyl sulfoxide / 1.5 h / 0 - 5 °C 2: ammonium hydroxide / isopropyl alcohol; water / 15 h / 20 °C

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US2012/95020, 2012, A1

27
[ 18385-87-0 ]
[ 1373215-15-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: N-Bromosuccinimide; water / dimethyl sulfoxide / 1.5 h / 0 - 5 °C 2.1: ammonium hydroxide / isopropyl alcohol; water / 15 h / 20 °C 3.1: D-(+)-camphoric acid / acetonitrile; water / 0.17 h / 70 - 75 °C 3.2: 50 °C 4.1: sodium hydrogencarbonate / water; tetrahydrofuran / 2.25 h / 17 °C / Industry scale 5.1: sodium t-butanolate / bis(η3-allyl-μ-chloropalladium(II)); tri tert-butylphosphoniumtetrafluoroborate / dimethyl sulfoxide / 0.75 h / 93 - 98 °C / Inert atmosphere 5.2: pH 2.3 5.3: 1 h / 40 °C 6.1: sodium tris(acetoxy)borohydride / acetonitrile / 5.67 h / 28 °C 7.1: tetrahydrofuran / 20 °C 7.2: 0.75 h / 5 °C
	Multi-step reaction with 7 steps 1.1: N-Bromosuccinimide; water / dimethyl sulfoxide / 1.5 h / 0 - 5 °C 2.1: ammonium hydroxide / isopropyl alcohol; water / 15 h / 20 °C 3.1: D-(+)-camphoric acid / acetonitrile; water / 0.17 h / 70 - 75 °C 3.2: 50 °C 4.1: sodium hydrogencarbonate / water; tetrahydrofuran / 2.25 h / 17 °C / Industry scale 5.1: sodium t-butanolate / bis(η3-allyl-μ-chloropalladium(II)); tri tert-butylphosphoniumtetrafluoroborate / toluene; dimethyl sulfoxide / 4 h / 70 °C / Inert atmosphere 5.2: 0.5 h / pH 6 - 7 5.3: pH 11 - 12 6.1: acetic acid / tetrahydrofuran / 1 h / 35 - 40 °C 6.2: 4 h / 35 - 40 °C 7.1: tetrahydrofuran / 20 °C 7.2: 0.75 h / 5 °C
	Multi-step reaction with 7 steps 1.1: N-Bromosuccinimide; water / dimethyl sulfoxide / 1.5 h / 0 - 5 °C 2.1: ammonium hydroxide / isopropyl alcohol; water / 15 h / 20 °C 3.1: CHIRALPAK_.(R). AD-H column / dimethyl amine; methanol / Resolution of racemate 4.1: sodium hydrogencarbonate / water; tetrahydrofuran / 2.25 h / 17 °C / Industry scale 5.1: sodium t-butanolate / bis(η3-allyl-μ-chloropalladium(II)); tri tert-butylphosphoniumtetrafluoroborate / dimethyl sulfoxide / 0.75 h / 93 - 98 °C / Inert atmosphere 5.2: pH 2.3 5.3: 1 h / 40 °C 6.1: sodium tris(acetoxy)borohydride / acetonitrile / 5.67 h / 28 °C 7.1: tetrahydrofuran / 20 °C 7.2: 0.75 h / 5 °C

Multi-step reaction with 7 steps 1.1: N-Bromosuccinimide; water / dimethyl sulfoxide / 1.5 h / 0 - 5 °C 2.1: ammonium hydroxide / isopropyl alcohol; water / 15 h / 20 °C 3.1: CHIRALPAK_.(R). AD-H column / dimethyl amine; methanol / Resolution of racemate 4.1: sodium hydrogencarbonate / water; tetrahydrofuran / 2.25 h / 17 °C / Industry scale 5.1: sodium t-butanolate / bis(η3-allyl-μ-chloropalladium(II)); tri tert-butylphosphoniumtetrafluoroborate / toluene; dimethyl sulfoxide / 4 h / 70 °C / Inert atmosphere 5.2: 0.5 h / pH 6 - 7 5.3: pH 11 - 12 6.1: acetic acid / tetrahydrofuran / 1 h / 35 - 40 °C 6.2: 4 h / 35 - 40 °C 7.1: tetrahydrofuran / 20 °C 7.2: 0.75 h / 5 °C

28
[ 49660-57-3 ]
[ 18385-87-0 ]

Reference： [1]Patent: US2012/95020,2012,A1
[2]Synthesis,2019,vol. 51,p. 848 - 858

29
[ 18385-87-0 ]
potassium 4-(methoxy)phenyltrifluoroborate [ No CAS ]
[ 1346936-72-8 ]

Yield	Reaction Conditions	Operation in experiment
97%	With triphenylmethyl perchlorate In dichloromethane for 2h; Inert atmosphere; chemoselective reaction;

Reference： [1]Chen, Wenfang; Xie, Zhiyu; Zheng, Hongbo; Lou, Hongxiang; Liu, Lei [Organic Letters, 2014, vol. 16, # 22, p. 5988 - 5991]

30
[ 18385-87-0 ]
[ 100-66-3 ]
[ 1346936-72-8 ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: 6-bromo-2H-benzopyran With triphenylmethyl perchlorate In dichloromethane at 20℃; Inert atmosphere; Stage #2: methoxybenzene In dichloromethane for 2h; Inert atmosphere; chemoselective reaction;
50%	With indium(III) triflate; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 20℃; for 5h;

Reference： [1]Chen, Wenfang; Xie, Zhiyu; Zheng, Hongbo; Lou, Hongxiang; Liu, Lei [Organic Letters, 2014, vol. 16, # 22, p. 5988 - 5991]
[2]Li, Fanmei; Meng, Zhilin; Hua, Jing; Li, Wei; Lou, Hongxiang; Liu, Lei [Organic and Biomolecular Chemistry, 2015, vol. 13, # 20, p. 5710 - 5715]

31
[ 33133-45-8 ]
[ 18385-87-0 ]

Yield	Reaction Conditions	Operation in experiment
70%	With indium (III) iodide In toluene at 100℃; for 24h; Schlenk technique; Inert atmosphere; regioselective reaction;

Reference： [1]Alonso-Maran, Lorena; Martnez, M. Montserrat; Sarandeses, Luis A.; Sestelo, Jos Prez [Organic and Biomolecular Chemistry, 2014, vol. 13, # 2, p. 379 - 387]

32
[ 1429628-96-5 ]
[ 18385-87-0 ]

Yield	Reaction Conditions	Operation in experiment
76%	With [2,2]bipyridinyl; iron(III) chloride In tetrahydrofuran at 20 - 80℃; for 5h; Microwave irradiation; Inert atmosphere;

Reference： [1]Calmus; Corbu; Cossy [Advanced Synthesis and Catalysis, 2015, vol. 357, # 7, p. 1381 - 1386]

33
[ 18385-87-0 ]
[ 13195-64-7 ]
diisopropyl 2-(6-bromo-2H-chromen-2-yl)malonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With indium(III) triflate; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 20℃; for 5h;

Reference： [1]Li, Fanmei; Meng, Zhilin; Hua, Jing; Li, Wei; Lou, Hongxiang; Liu, Lei [Organic and Biomolecular Chemistry, 2015, vol. 13, # 20, p. 5710 - 5715]

34
C₉H₈BrOPolSe [ No CAS ]
[ 18385-87-0 ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide In tetrahydrofuran; water at 0 - 20℃; for 1.33h;	21 Polystyrene-supported selenium allyl ether (1.0g, 0.97mmol), in anhydrous dichloromethane (10 mL) Set the reaction flask was allowed to stand at room temperature for 4h, until swelling of the resin, at -10 ° C was added N- chlorosuccinimide (0.4g, 3.0 mmol), - 10 ° C under stirring and stirring was continued at room temperature for 48h after 24h. Reaction to complete, filtered through a sand core funnel, With dry dichloromethane (4 × 10mL) washing, polystyrene-supported selenium succinimide . Now the resulting resin continues with dried dichloromethane (10 mL) soaking, cooled down to -78 ° C, was added trifluoromethanesulfonic acid trimethylsilyl ester (0.011 g, 0.05mmol), stirred at -78 ° C the reaction 0.5h. Phenyl cinnamate ether-based compound (1.066g, 5.0mmol), Stirring was continued at -78 ° C reaction 2h, the reaction mixture was placed under 3.5h -20 ° C. Reaction to complete, adding bicarbonate Saturated sodium solution (5mL), washed with dichloromethane (3 × 10mL), water (3 × 10mL), tetrahydrofuran + water (V / V = 1: 1, 3 × 10mL), tetrahydrofuran (3 × 10mL), ethanol (3 × 10mL), methanol (3 × 10mL), diethyl ether (3 × 10mL), In dichloromethane (10 mL), acetone (3 × 10mL), tetrahydrofuran (10mL) and washed resin, polystyrene load to give 3- Selenium benzopyran-6-bromo -2H- . The combined filtrate and washings. Recovered most of the solvent, the residue was extracted with ethyl acetate, The combined organic layer was dried over anhydrous sodium sulfate. After recovering the solvent, the reaction was recovered cinnamic phenyl ether-based compound 0.56 g. The compound () set reaction flask with tetrahydrofuran (15mL) at room temperature soak 4h. Cooled in an ice bath to 0° C, was added 30% aqueous hydrogen peroxide 1.2mL, 0 ° C The reaction was stirred 1h, slowly warmed to room temperature, and stirring was continued reaction 20min. Reaction to complete, filtered through a sand core funnel with dichloromethane (4 × 10mL) and washed resin. The combined filtrate and washings, Was added water (5mL) and saturated aqueous sodium bisulfite (5mL) removing excess hydrogen peroxide. The organic layer was separated, washed with water (5mL). The aqueous layer (2 × 5mL) and extracted with dichloromethane. The combined organic layer was dried over anhydrous sodium sulfate, solvent recovery Agent, to give 6-bromo- -2H- benzopyran (yield 0.169g, 80%, a purity of greater than 90%).

Reference： [1]Current Patent Assignee: YUNNAN UNIVERSITY - CN105399718, 2016, A Location in patent: Paragraph 0055

35
[ 18385-87-0 ]
[ 64-17-5 ]
[ 116486-26-1 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; Inert atmosphere;

Reference： [1]Yang, Fei; Li, Yangshan; Floreancig, Paul E.; Li, Xiaoyan; Liu, Lei [Organic and Biomolecular Chemistry, 2018, vol. 16, # 28, p. 5144 - 5149]

36
[ 18385-87-0 ]
C₇H₇BrZn*MgCl₂*LiCl [ No CAS ]
6-bromo-2-(o-tolyl)-2H-chromene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: 6-bromo-2H-benzopyran With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 80℃; for 2h; Schlenk technique; Inert atmosphere; Stage #2: C₇H₇BrZnMgCl₂LiCl In 1,2-dichloro-ethane at 20℃;

Reference： [1]Peng, Zhihua; Wang, Yilei; Yu, Zhi; Zhao, Dezhi; Song, Linhua; Jiang, Cuiyu [Journal of Organic Chemistry, 2018, vol. 83, # 15, p. 7900 - 7906]

37
[ 18385-87-0 ]
2-(6-bromo-2H-chromen-2-yl)pentan-1-ol [ No CAS ]
2-(6-bromo-2H-chromen-2-yl)pentan-1-ol [ No CAS ]
2-(6-bromo-2H-chromen-2-yl)pentan-1-ol [ No CAS ]
2-(6-bromo-2H-chromen-2-yl)pentan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: o-tetrachloroquinone / dichloromethane / 20 °C 2.1: (5S)-5-benzyl-2,2,3-trimethylimidazolidin-4-one trifluoroacetic acid salt; lithium trifluoromethanesulfonate; water / dichloromethane / 0 °C 2.2: 0.33 h / 0 °C

Reference： [1]Pan, Xinhui; Liu, Xigong; Sun, Shutao; Meng, Zhilin; Liu, Lei [Chinese Journal of Chemistry, 2018, vol. 36, # 12, p. 1187 - 1190]

38
[ 18385-87-0 ]
C₉H₇BrO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With o-tetrachloroquinone In dichloromethane at 20℃;

Reference： [1]Pan, Xinhui; Liu, Xigong; Sun, Shutao; Meng, Zhilin; Liu, Lei [Chinese Journal of Chemistry, 2018, vol. 36, # 12, p. 1187 - 1190]

39
[ 18385-87-0 ]
cis-6-bromo-4-methoxychroman-3-sulfonyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: N-Bromosuccinimide / 20 - 30 °C 2: N,N-dimethyl-formamide / 48 h / 110 °C 3: N-chloro-succinimide; hydrogenchloride; water / acetonitrile / 10 - 20 °C

40
[ 18385-87-0 ]
C₁₂H₁₃BrO₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-Bromosuccinimide / 20 - 30 °C 2: N,N-dimethyl-formamide / 48 h / 110 °C

41
[ 67-56-1 ]
[ 18385-87-0 ]
trans-3,6-dibromo-4-methoxychroman [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With N-Bromosuccinimide at 20 - 30℃; diastereoselective reaction;	β-Methoxybromides 2a, 2b, 6a-e, and 6g-j; General Procedure General procedure: To a solution of alkene 5 (1 mol) in anhyd MeOH (1 L) was added NBS (187 g, 1.05 mol) portionwise while maintaining the temperature below 30 °C. After the addition of all the NBS, the reaction mixture was stirred at r.t. overnight. The resulting mixture was evaporated under reduced pressure; H2O (1 L) was added, and the mixture was extracted with CH2Cl2(3300 mL). The combined organic phases were washed with H2O (2300 mL), 10% aq NaHSO3(2300 mL), H2O (2300 mL), dried (anhyd Na2SO4), and evaporated under reduced pressure.

42
[ 18385-87-0 ]
[ 73183-34-3 ]
C₁₅H₂₀BBrO₃ [ No CAS ]
C₁₅H₂₀BBrO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: bis(pinacol)diborane With (1S,1S',2R,2R')-2,2'-di-tert-butyl-2,3,2',3'-tetrahydro-1H,1H'-[1,1']biisophosphindolyl; potassium methanolate; copper(l) chloride In tetrahydrofuran at -20℃; for 0.333333h; Inert atmosphere; Schlenk technique; Stage #2: 6-bromo-2H-benzopyran With methanol In tetrahydrofuran at -20 - 20℃; for 6h; Inert atmosphere; Schlenk technique; Overall yield = 65 percent; Overall yield = 55 mg; Optical yield = 64 percent ee;

Reference： [1]Li, Xiufen; Wang, Chaoqiong; Song, Jianqiao; Yang, Zhihong; Zi, Guofu; Hou, Guohua [Journal of Organic Chemistry, 2019, vol. 84, # 13, p. 8638 - 8645]

43
[ 93670-18-9 ]
[ 18385-87-0 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminum (III) chloride at 0℃; for 1h;

Reference： [1]Li, Xiufen; Wang, Chaoqiong; Song, Jianqiao; Yang, Zhihong; Zi, Guofu; Hou, Guohua [Journal of Organic Chemistry, 2019, vol. 84, # 13, p. 8638 - 8645]

44
[ 106-41-2 ]
[ 18385-87-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium hydroxide / water / 12 h / 75 - 80 °C 2: aluminum (III) chloride / 1 h / 0 °C

Reference： [1]Li, Xiufen; Wang, Chaoqiong; Song, Jianqiao; Yang, Zhihong; Zi, Guofu; Hou, Guohua [Journal of Organic Chemistry, 2019, vol. 84, # 13, p. 8638 - 8645]

45
C₁₄H₁₇BrO₂ [ No CAS ]
[ 18385-87-0 ]
[ 96-22-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	With 2,3-diazabicyclo[2.2.1]heptane bis-trifluoroacetic acid In ethanol at 140℃; for 12h; Sealed tube;

Reference： [1]Jermaks, Janis; Lambert, Tristan H.; Macmillan, Samantha N.; Zhang, Yunfei [ACS Catalysis, 2019, p. 9259 - 9264]

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P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 18385-87-0 ] {[proInfo.proName]}

Quality Control of [ 18385-87-0 ]

Related Doc. of [ 18385-87-0 ]

Product Details of [ 18385-87-0 ]

Calculated chemistry of [ 18385-87-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 18385-87-0 ]

Application In Synthesis of [ 18385-87-0 ]

[ 18385-87-0 ] Synthesis Path-Upstream 1~1

[ 18385-87-0 ] Synthesis Path-Downstream 1~45

Related Functional Groups of [ 18385-87-0 ]

Bromides

Related Parent Nucleus of [ 18385-87-0 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 18385-87-0 ]

Related Parent Nucleus of
[ 18385-87-0 ]