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Chemical Structure| 60633-25-2
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Product Details of [ 60633-25-2 ]

CAS No. :60633-25-2 MDL No. :MFCD00079705
Formula : C7H6BrClO Boiling Point : -
Linear Structure Formula :- InChI Key :YJEMGEBDXDPBSP-UHFFFAOYSA-N
M.W : 221.48 Pubchem ID :521935
Synonyms :

Calculated chemistry of [ 60633-25-2 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.64
TPSA : 9.23 Ų

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) : -5.36 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.46
Log Po/w (XLOGP3) : 3.22
Log Po/w (WLOGP) : 3.11
Log Po/w (MLOGP) : 3.15
Log Po/w (SILICOS-IT) : 3.14
Consensus Log Po/w : 3.01

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.62
Solubility : 0.0532 mg/ml ; 0.00024 mol/l
Class : Soluble
Log S (Ali) : -3.09
Solubility : 0.182 mg/ml ; 0.00082 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.0
Solubility : 0.0221 mg/ml ; 0.0001 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.53

Safety of [ 60633-25-2 ]

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 [ 60633-25-2 ]

* 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.

  • Upstream synthesis route of [ 60633-25-2 ]
  • Downstream synthetic route of [ 60633-25-2 ]

[ 60633-25-2 ] Synthesis Path-Upstream   1~17

  • 1
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Reference: [1] Journal of the American Chemical Society, 1950, vol. 72, p. 830
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  • [ 3743-23-5 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1944, vol. <5> 11, p. 505,509
  • 3
  • [ 121-43-7 ]
  • [ 60633-25-2 ]
  • [ 89694-48-4 ]
YieldReaction ConditionsOperation in experiment
77% With n-butyllithium In (5-fluoro-2-methoxyphenyl)boronic acid 5-Chloro-2-methoxyphenylboronic acid (structure 37 of Scheme XI, where R1 =H, R2 =Cl)
This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 2-bromo-4-chloroanisole (2.00 g, 9.0 mmol, 1.0 equivuiv), n-BuLi (2.5M in hexanes; 3.62 mL, 9.0 mmol, 1.0 equivuiv), and trimethylborate (3.0 mL, 26 mmol, 2.9 equivuiv) to afford 1.30 g (77percent) of crude 5-chloro-2-methoxyphenylboronic acid as a white semi-solid.
This compound was used in the next reaction with no further purification.
Methyl (5'-chloro-2'-methoxy-4-nitro-2-biphenyl)carboxylate (structure 39 of Scheme XI, where R1 =H, R2 =Cl)
77% With n-butyllithium In (5-fluoro-2-methoxyphenyl)boronic acid 5-Chloro-2-methoxyphenylboronic acid (structure 37 of Scheme XI, where R1 =H, R2 =Cl)
This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 2-bromo-4-chloroanisole (2.00 g, 9.0 mmol, 1.0 equivuiv), n-BuLi (2.5M in hexanes; 3.62 mL, 9.0 mmol, 1.0 equivuiv), and trimethylborate (3.0 mL, 26 mmol, 2.9 equivuiv) to afford 1.30 g (77percent) of crude 5-chloro-2-methoxyphenylboronic acid as a white semi-solid.
This compound was used in the next reaction with no further purification.
Methyl (5'-chloro-2'-methoxy-4-nitro-2-biphenyl)carboxylate (structure 39 of Scheme XI, where R1 =H, R2 =Cl)
77% With n-butyllithium In (5-fluoro-2-methoxyphenyl)boronic acid 5-Chloro-2-methoxyphenylboronic acid (structure 37 of Scheme XI, where R1 =H, R2 =Cl)
This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 2-bromo-4-chloroanisole (2.00 g, 9.0 mmol, 1.0 equivuiv), n-BuLi (2.5M in hexanes; 3.62 mL, 9.0 mmol, 1.0 equivuiv), and trimethylborate (3.0 mL, 26 mmol, 2.9 equivuiv) to afford 1.30 g (77percent) of crude 5-chloro-2-methoxyphenylboronic acid as a white semi-solid.
This compound was used in the next reaction with no further purification.
Methyl(5'-chloro-2'-methoxy-4-nitro-2-biphenyl)carboxylate (structure 39 of Scheme XI, where R1 =H, R2 =Cl)
77% With n-butyllithium In (5-fluoro-2-methoxyphenyl)boronic acid 5-Chloro-2-methoxyphenylboronic acid (structure 37 of Scheme XI where R1 =H, R2 =Cl)
This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 2-bromo-4-chloroanisole (2.00 g, 9.01 mmol, 1.0 equivuiv), n-BuLi (2.5M in hexanes; 3.62 mL, 9.01 mmol, 1.0 equivuiv), and trimethylborate (3.0 mL, 26 mmol, 2.9 equivuiv) to afford 1.30 g (77percent) of crude 5-chloro-2-methoxyphenylboronic acid as a white semi-solid.
This compound was used in the next reaction with no further purification.
Methyl (5'-chloro-2'-methoxy-4-nitro-2-biphenyl)carboxylate (structure 39 of Scheme XI, where R1 =H, R2 =Cl)
77% With n-butyllithium In (5-fluoro-2-methoxyphenyl)boronic acid 5-Chloro-2-methoxyphenylboronic acid (structure 37 of Scheme XI, where R1 =H, R2 =Cl) This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 2-bromo-4-chloroanisole (2.00 g, 9.0 mmol, 1.0 equivuiv), n-BuLi (2.5M in hexanes; 3.62 mL, 9.0 mmol, 1.0 equivuiv), and trimethylborate (3.0 mL, 26 mmol, 2.9 equivuiv) to afford 1.30 g (77percent) of crude 5-chloro-2-methoxyphenylboronic acid as a white semi-solid.
This compound was used in the next reaction with no further purification.

Reference: [1] Patent: US5688808, 1997, A,
[2] Patent: US5688810, 1997, A,
[3] Patent: US5693646, 1997, A,
[4] Patent: US5693647, 1997, A,
[5] Patent: US5696127, 1997, A,
[6] Patent: US5696133, 1997, A,
[7] Patent: US5696130, 1997, A,
  • 4
  • [ 5419-55-6 ]
  • [ 60633-25-2 ]
  • [ 89694-48-4 ]
Reference: [1] Patent: US5534518, 1996, A,
  • 5
  • [ 688-74-4 ]
  • [ 60633-25-2 ]
  • [ 89694-48-4 ]
Reference: [1] Patent: US6207662, 2001, B1,
  • 6
  • [ 60633-25-2 ]
  • [ 89694-48-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 17, p. 6626 - 6637
  • 7
  • [ 695-96-5 ]
  • [ 77-78-1 ]
  • [ 60633-25-2 ]
YieldReaction ConditionsOperation in experiment
99% With sodium hydroxide In dichloromethane; water at 20℃; for 22 h; 2-Bromo-4-chloro-1-methoxybenzene (47). A solution of sodium hydroxide (836 mg, 20.9 mmol) in water (8.0 mL) was added to a solution of 2-bromo-4-chlorophenol (45) (2.1 g, 9.92 mmol) and tetrabutylammonium bromide (336.4 mg, 1.03 mmol) in dichloromethane. Dimethyl sulfate (1.5 mL, 15.69 mmol) was added. The resulting mixture was stirred at room temperature for 22 h and then 1 N aq HCl (about 2 mL) was added to quench the reaction. The organic phase was separated and the aqueous phase was extracted with dichloromethane (2.x.15 mL). The combined organic phase was washed with brine, dried over sodium sulfate and concentrated to afford an oil. The crude product was purified by column chromatography on silica gel (10 g) using EtOAc-hexanes (5percent) to afford the product 47 as a colorless oil (2.17 g) in 99percent yield. See, Dischino, D. D.; Gribkoff, V. K.; Hewawasam, P.; Luke, G. M.; Rinehart, J. K.; Spears, T. L.; Starrett Jr, J. E. Synthesis of 3H and 14 C Labeled (S)-3-(5-Chloro-2-methoxyphenyl)-1,3-dihydro-3-fluoro-6-(trifluoromethyl)-2H-indol-2-one, Maxipost.(TM).. An Agent for Post-Stroke Neuroprotection. J. Label. Compd. Radiopharm. 2003, 46, 139-149, the disclosure of which is incorporated herein by reference. 1H NMR (300 MHz, CDCl3) δ 7.51 (d, J=2.4 Hz, 1H), 7.22 (dd, J=2.4 Hz, J=8.7 Hz, 1H), 6.80 (d, J=8.7 Hz, 1H), 3.86 (s, 3H).
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 6140 - 6155
[2] Patent: US2008/300288, 2008, A1, . Location in patent: Page/Page column 23; 10
[3] Journal of Labelled Compounds and Radiopharmaceuticals, 2003, vol. 46, # 2, p. 139 - 149
[4] Journal of the American Chemical Society, 2005, vol. 127, # 29, p. 10164 - 10165
  • 8
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  • [ 74-88-4 ]
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YieldReaction ConditionsOperation in experiment
96% With potassium carbonate In acetone for 6 h; Reflux General procedure: To a stirred solution of 7aa (19.11 g, 0.10 mol) or 7ab (20.75 g, 0.10 mol) in acetone (150 mL) was added K2CO3 (13.80 g, 0.10 mol) and MeI (12.61, 0.10 mol) at room temperature. After the mixture being refluxed for 6 h, the solvent was evaporated under reduced pressure and the residue was poured into H2O (150 mL) and extracted with CH2Cl2 (2 .x. 100 mL). The combined organic layer was washed with H2O (2 .x. 100 mL) and dried with anhydrous NaSO4. The solvent was evaporated to afford light yellow oil 8aa (94percent) or 8ab (96percent).
98% With potassium carbonate In water; acetone EXAMPLE 109
9-Chloro-1,2-dihydro-2,2,4-trimethyl-5-coumarino[3,4-f]quinoline (Compound 209, structure 41 of Scheme XI, where R1 =H, R2 =Cl)
2-Bromo-4-chloroanisole (structure 36 of Scheme XI, where R1 =H, R2 =Cl) In a 250 mL r.b. flask, a solution of 2-bromo-4-chlorophenol (Lancaster: 16.94 g, 81.6 mmol, 1.0 equivuiv) in acetone (160 mL) was treated sequivuentially with iodomethane (6.10 mL, 98 mmol, 1.2 equivuiv), potassium carbonate (12 g), and water (4 mL).
The reaction mixture was heated at reflux for 3 h, cooled to rt, and the bulk of the volatiles was removed under reduced pressure.
The residue was poured into water (140 mL) and extracted with EtOAc (3*150 mL).
The extracts were washed with brine (1*100 mL), combined, dried (K2 CO3), filtered through a pad of Celite.(TM)., and concentrated to a clear oil. Short-path distillation (80°-85° C., 1 Torr) afforded 17.74 g (98percent) of 2-bromo-4-chloroanisole as a clear liquid.
Data for 2-bromo-4-chloroanisole: 1 H NMR (400 MHz, acetone-d6) 7.53 (d, J=2.5, 1H); 7.24 (dd, J=9.7, 2.5, 1H); 6.81 (d, J=9.7, 1H); 3.88 (s, 3H).
98% With potassium carbonate In water; acetone EXAMPLE 109
9-Chloro-1,2-dihydro-2,2,4-trimethyl-5-coumarino[3,4-f]quinoline (Compound 209, structure 41 of Scheme XI, where R1 =H, R2 =Cl)
2-Bromo-4-chloroanisole (structure 36 of Scheme XI, where R1 =H, R2 =Cl) In a 250 mL r.b. flask, a solution of 2-bromo-4-chlorophenol (Lancaster: 16.94 g, 81.6 mmol, 1.0 equivuiv) in acetone (160 mL) was treated sequivuentially with iodomethane (6.10 mL, 98 mmol, 1.2 equivuiv), potassium carbonate (12 g), and water (4 mL).
The reaction mixture was heated at reflux for 3 h, cooled to rt, and the bulk of the volatiles was removed under reduced pressure.
The residue was poured into water (140 mL) and extracted with EtOAc (3*150 mL).
The extracts were washed with brine (1*100 mL), combined, dried (K2 CO3), filtered through a pad of Celite.(TM)., and concentrated to a clear oil. Short-path distillation (80°-85° C., 1 Torr) afforded 17.74 g (98percent) of 2-bromo-4-chloroanisole as a clear liquid.
Data for 2-bromo-4-chloroanisole: 1 H NMR (400 MHz, acetone-d6) 7.53 (d, J=2.5, 1 H); 7.24 (dd, J=9.7, 2.5, 1 H); 6.81 (d, J=9.7, 1 H); 3.88 (s, 3 H).
Reference: [1] Angewandte Chemie - International Edition, 2008, vol. 47, # 27, p. 5067 - 5070
[2] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 14, p. 4220 - 4226
[3] Angewandte Chemie - International Edition, 2014, vol. 53, # 25, p. 6443 - 6448[4] Angew. Chem., 2014, vol. 126, # 25, p. 6561 - 6566
[5] Patent: US5688808, 1997, A,
[6] Patent: US5696133, 1997, A,
[7] Patent: US5696130, 1997, A,
[8] Patent: US2006/287303, 2006, A1, . Location in patent: Page/Page column 84-85; 87-89
  • 9
  • [ 1583286-02-5 ]
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YieldReaction ConditionsOperation in experiment
89% With bromine In dichloromethane at 0 - 23℃; for 1 h; [001171 2-Bl'Omo-4-chloro-1-methoxybenzene (54) (Hamashima, N a/., J. Am. Chern. Soc.127:10 J 64-10165 (2005;;: To a solution of l6b (151 mg, 0.416 mmol) in CH2Cl2 (5 mL) wasadded bruminc (100 mg, 0.626 mmol) at 0 °C, and the reaction mixture was stirred at 23 ocfor 1 h. The reaction was then quenched witl1 Na2S201 (30percent aqueous solution, 2 rnL) at 0oc. The aqueous phase was extracted with ethyl acetate. the combined organic layer wasdried over MgS04, filtered. and tl1e solvent was evaporated in vacuo. The residue waspurified by flash colunrn chromatography (0-710percent ethyl acetate in hexane:>) to give theproduct as a colorless liquid (8 l .6 rng. 89percent yield). 1H NMR (600 Mfiz, CDCh) o 7.53 (d . .J=2.4Hz,IH),7.24(dd,J=8.8,2.4Hz, IHJ,6.81 (d,J=8.8Hz, IH),3.87(s,3H). t.lCNMR (151 MHz, CDCb) o 154.87 (s), 132.93 (s), 128.41 (s), 126.07 (:>), 112.64 (s), 112.23(s). 56.58 (s).
Reference: [1] Science, 2014, vol. 343, # 6173, p. 853 - 857
[2] Patent: WO2015/35325, 2015, A1, . Location in patent: Paragraph 00117
  • 10
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YieldReaction ConditionsOperation in experiment
95% With N-Bromosuccinimide; iodine In acetonitrile at 35℃; for 6 h; Darkness To a reaction tube charged with NBS (1.5 equiv, 0.3 mmol), catalyst (10 molpercent, 0.02 mmol) and CH3CN (1.0 mL),was added para-chloroanisole 1a (0.2 mmol). After being stirred at room temperature for 12 h in dark, the reaction was quenched by saturated aq. solution of Na2S2O3 (2 mL). The resulting mixture was extracted by ethyl acetate (3 5 mL). The combined organic extracts were washed by brine (10 mL), dried over Na2SO4 and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure and the residuewas purified by flash chromatography on a silica gel column with petroleum ether/dichloromethane (5:1) as the eluent to give 4.3.1. 2-Bromo-4-chloroanisole (2a) 42.0 mg, 95percent yield. 1H NMR (400 MHz, CDCl3) δ 7.53 (d, J = 2.4 Hz, 1H), 7.24 (dd, J = 8.6, 2.3 Hz, 1H), 6.82 (d, J = 8.8 Hz, 1H), 3.88 (s, 3H). The NMR data is in good agreement with that reported in the literature.29
Reference: [1] Helvetica Chimica Acta, 1983, vol. 66, # 4, p. 1068 - 1077
[2] Helvetica Chimica Acta, 1983, vol. 66, # 4, p. 1068 - 1077
[3] Chemistry - A European Journal, 2017, vol. 23, # 5, p. 1044 - 1047
[4] Tetrahedron, 2017, vol. 73, # 50, p. 7105 - 7114
[5] Journal of Organic Chemistry, 2018, vol. 83, # 2, p. 930 - 938
[6] Monatshefte fur Chemie, 2013, vol. 144, # 2, p. 179 - 181
[7] International Journal of Chemical Kinetics, 2016, vol. 48, # 2, p. 98 - 105
[8] Bulletin de la Societe Chimique de France, 1981, vol. 1, # 1-2, p. 42 - 48
[9] Journal of the Indian Chemical Society, 1983, vol. 60, p. 953 - 957
[10] Bulletin de la Societe Chimique de France, 1944, vol. <5> 11, p. 505,509
[11] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1942, vol. 214, p. 910[12] Bulletin de la Societe Chimique de France, 1944, vol. <5> 11, p. 505,510
[13] Science, 2014, vol. 343, # 6173, p. 853 - 857
[14] Synlett, 2014, vol. 25, # 12, p. 1769 - 1775
[15] Organic Letters, 2015, vol. 17, # 5, p. 1122 - 1125
[16] Journal of Organic Chemistry, 2017, vol. 82, # 14, p. 7529 - 7537
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YieldReaction ConditionsOperation in experiment
98% With potassium carbonate In water; acetone EXAMPLE 109
9-Chloro-1,2-dihydro-2,2,4-trimethyl-5-coumarino[3,4-f]quinoline (Compound 209, structure 41 of Scheme XI, where R1 =H, R2 =Cl)
2-Bromo-4-chloroanisole (structure 36 of Scheme XI, where R1 =H, R2 =Cl)
In a 250 mL r.b. flask, a solution of 2-bromo-4-chlorophenol (Lancaster: 16.94 g, 81.6 mmol, 1.0 equivuiv) in acetone (160 mL) was treated sequivuentially with iodomethane (6.10 mL, 98 mmol, 1.2 equivuiv), potassium carbonate (12 g), and water (4 mL).
The reaction mixture was heated at reflux for 3 h, cooled to rt, and the bulk of the volatiles was removed under reduced pressure.
The residue was poured into water (140 mL) and extracted with EtOAc (3*150 mL).
The extracts were washed with brine (1*100 mL), combined, dried (K2 CO3), filtered through a pad of Celite.(TM)., and concentrated to a clear oil. Short-path distillation (80°-85° C., 1 Torr) afforded 17.74 g (98percent) of 2-bromo-4-chloroanisole as a clear liquid.
Data for 2-bromo-4-chloroanisole:
1 H NMR (400 MHz, acetone-d6) 7.53 (d, J=2.5, 1H); 7.24 (dd, J=9.7, 2.5, 1H); 6.81 (d, J=9.7, 1H); 3.88 (s, 3H).
98% With potassium carbonate In water; acetone EXAMPLE 109
9-Chloro-1,2-dihydro-2,2,4-trimethyl-5-coumarino[3,4-f]quinoline (Compound 209, structure 41 of Scheme XI, where R1 =H, R2 =Cl)
2-Bromo-4-chloroanisole (structure 36 of Scheme XI, where R1 =H, R2 =Cl)
In a 250 mL r.b. flask, a solution of 2-bromo-4-chlorophenol (Lancaster: 16.94 g, 81.6 mmol, 1.0 equivuiv) in acetone (160 mL) was treated sequivuentially with iodomethane (6.10 mL, 98 mmol, 1.2 equivuiv), potassium carbonate (12 g), and water (4 mL).
The reaction mixture was heated at reflux for 3 h, cooled to rt, and the bulk of the volatiles was removed under reduced pressure.
The residue was poured into water (140 mL) and extracted with EtOAc (3*150 mL).
The extracts were washed with brine (1*100 mL), combined, dried (K2 CO3), filtered through a pad of Celite.(TM)., and concentrated to a clear oil. Short-path distillation (80°-85° C., 1 Torr) afforded 17.74 g (98percent) of 2-bromo-4-chloroanisole as a clear liquid.
Data for 2-bromo-4-chloroanisole: 1 H NMR (400 MHz, acetone-d6) 7.53 (d, J=2.5, 1 H); 7.24 (dd, J=9.7, 2.5, 1 H); 6.81 (d, J=9.7, 1 H); 3.88 (s, 3 H).
98% With potassium carbonate In water; acetone EXAMPLE 109
9-Chloro-1,2-dihydro-2,2,4-trimethyl-5-coumarino[3,4-f]quinoline (Compound 209, structure 41 of Scheme XI, where R1 =H, R2 =Cl)
2-Bromo-4-chloroanisole (structure 36 of Scheme XI, where R1 =H, R2 =Cl)
In a 250 mL r.b. flask, a solution of 2-bromo-4-chlorophenol (Lancaster: 16.94 g, 81.6 mmol, 1.0 equivuiv) in acetone (160 mL) was treated sequivuentially with iodomethane (6.10 mL, 98 mmol, 1.2 equivuiv), potassium carbonate (12 g), and water (4 mL).
The reaction mixture was heated at reflux for 3 h, cooled to rt, and the bulk of the volatiles was removed under reduced pressure.
The residue was poured into water (140 mL) and extracted with EtOAc (3*150 mL).
The extracts were washed with brine (1*100 mL), combined, dried (K2 CO3), filtered through a pad of Celite.(TM)., and concentrated to a clear oil. Short-path distillation (80°-85° C., 1 Torr) afforded 17.74 g (98percent) of 2-bromo-4-chloroanisole as a clear liquid.
Data for 2-bromo-4-chloroanisole: 1 H NMR (400 MHz, acetone-d6) 7.53 (d, J=2.5, 1H); 7.24 (dd, J=9.7, 2.5, 1H); 6.81 (d, J=9.7, 1H); 3.88 (s, 3H).
98% With potassium carbonate In water; acetone EXAMPLE 109
9-Chloro-1,2-dihydro-2,2,4-trimethyl-5-coumarino[3,4-f]quinoline (Compound 209, structure 41 of Scheme XI, where R1 =H, R2 =Cl)
2-Bromo-4-chloroanisole (structure 36 of Scheme XI, where R1 =H, R2 =Cl)
In a 250 mL r.b. flask, a solution of 2-bromo-4-chlorophenol (Lancaster: 16.94 g, 81.6 mmol, 1.0 equivuiv) in acetone (160 mL) was treated sequivuentially with iodomethane (6.10 mL, 98 mmol, 1.2 equivuiv), potassium carbonate (12 g), and water (4 mL).
The reaction mixture was heated at reflux for 3 h, cooled to rt, and the bulk of the volatiles was removed under reduced pressure.
The residue was poured into water (140 mL) and extracted with EtOAc (3*150 mL).
The extracts were washed with brine (1*100 mL), combined, dried (K2 CO3), filtered through a pad of Celite.(TM)., and concentrated to a clear oil. Short-path distillation (80°-85° C., 1 Torr) afforded 17.74 g (98percent) of 2-bromo-4-chloroanisole as a clear liquid.
Data for 2-bromo-4-chloroanisole: 1 H NMR (400 MHz, acetone-d6) 7.53 (d, J=2.5, 1H); 7.24 (dd, J=9.7, 2.5, 1H); 6.81 (d, J =9.7, 1H); 3.88 (s, 3H).

Reference: [1] Patent: US5688810, 1997, A,
[2] Patent: US5693646, 1997, A,
[3] Patent: US5693647, 1997, A,
[4] Patent: US5696127, 1997, A,
  • 12
  • [ 911302-20-0 ]
  • [ 60633-25-2 ]
Reference: [1] Tetrahedron, 2017, vol. 73, # 50, p. 7105 - 7114
  • 13
  • [ 695-96-5 ]
  • [ 60633-25-2 ]
Reference: [1] Patent: US5534518, 1996, A,
  • 14
  • [ 3438-16-2 ]
  • [ 60633-25-2 ]
Reference: [1] Chemical Science, 2018, vol. 9, # 15, p. 3860 - 3865
  • 15
  • [ 695-96-5 ]
  • [ 67-68-5 ]
  • [ 60633-25-2 ]
Reference: [1] Chemosphere, 2001, vol. 45, # 8, p. 1119 - 1127
  • 16
  • [ 578-57-4 ]
  • [ 60633-25-2 ]
Reference: [1] Chemical Science, 2017, vol. 8, # 10, p. 7009 - 7013
  • 17
  • [ 100-66-3 ]
  • [ 60633-25-2 ]
Reference: [1] Synlett, 2014, vol. 25, # 12, p. 1769 - 1775
[2] Journal of Organic Chemistry, 2017, vol. 82, # 14, p. 7529 - 7537
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[ 60633-25-2 ]

Aryls

Chemical Structure| 695-96-5

[ 695-96-5 ]

2-Bromo-4-chlorophenol

Similarity: 0.90

Chemical Structure| 174913-12-3

[ 174913-12-3 ]

1-Bromo-3-chloro-5-methoxybenzene

Similarity: 0.88

Chemical Structure| 2732-80-1

[ 2732-80-1 ]

2-Bromo-1-chloro-4-methoxybenzene

Similarity: 0.86

Chemical Structure| 50638-46-5

[ 50638-46-5 ]

4-Bromo-3-chloroanisole

Similarity: 0.86

Chemical Structure| 1214348-81-8

[ 1214348-81-8 ]

2-Bromo-4-chloro-1-(difluoromethoxy)benzene

Similarity: 0.86

Bromides

Chemical Structure| 695-96-5

[ 695-96-5 ]

2-Bromo-4-chlorophenol

Similarity: 0.90

Chemical Structure| 174913-12-3

[ 174913-12-3 ]

1-Bromo-3-chloro-5-methoxybenzene

Similarity: 0.88

Chemical Structure| 2732-80-1

[ 2732-80-1 ]

2-Bromo-1-chloro-4-methoxybenzene

Similarity: 0.86

Chemical Structure| 50638-46-5

[ 50638-46-5 ]

4-Bromo-3-chloroanisole

Similarity: 0.86

Chemical Structure| 1214348-81-8

[ 1214348-81-8 ]

2-Bromo-4-chloro-1-(difluoromethoxy)benzene

Similarity: 0.86

Chlorides

Chemical Structure| 695-96-5

[ 695-96-5 ]

2-Bromo-4-chlorophenol

Similarity: 0.90

Chemical Structure| 174913-12-3

[ 174913-12-3 ]

1-Bromo-3-chloro-5-methoxybenzene

Similarity: 0.88

Chemical Structure| 2732-80-1

[ 2732-80-1 ]

2-Bromo-1-chloro-4-methoxybenzene

Similarity: 0.86

Chemical Structure| 50638-46-5

[ 50638-46-5 ]

4-Bromo-3-chloroanisole

Similarity: 0.86

Chemical Structure| 1214348-81-8

[ 1214348-81-8 ]

2-Bromo-4-chloro-1-(difluoromethoxy)benzene

Similarity: 0.86

Ethers

Chemical Structure| 174913-12-3

[ 174913-12-3 ]

1-Bromo-3-chloro-5-methoxybenzene

Similarity: 0.88

Chemical Structure| 2732-80-1

[ 2732-80-1 ]

2-Bromo-1-chloro-4-methoxybenzene

Similarity: 0.86

Chemical Structure| 50638-46-5

[ 50638-46-5 ]

4-Bromo-3-chloroanisole

Similarity: 0.86

Chemical Structure| 1214348-81-8

[ 1214348-81-8 ]

2-Bromo-4-chloro-1-(difluoromethoxy)benzene

Similarity: 0.86

Chemical Structure| 174913-09-8

[ 174913-09-8 ]

1-Bromo-4-chloro-2-methoxybenzene

Similarity: 0.85