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Product Details of [ 76283-09-5 ]

CAS No. :76283-09-5 MDL No. :MFCD00055467
Formula : C7H5Br2F Boiling Point : -
Linear Structure Formula :- InChI Key :XMHNLZXYPAULDF-UHFFFAOYSA-N
M.W : 267.92 Pubchem ID :2733660
Synonyms :

Calculated chemistry of [ 76283-09-5 ]

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 : 46.94
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.61 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.49
Log Po/w (XLOGP3) : 3.27
Log Po/w (WLOGP) : 3.75
Log Po/w (MLOGP) : 4.25
Log Po/w (SILICOS-IT) : 3.93
Consensus Log Po/w : 3.54

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.94
Solubility : 0.0308 mg/ml ; 0.000115 mol/l
Class : Soluble
Log S (Ali) : -2.94
Solubility : 0.304 mg/ml ; 0.00114 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.79
Solubility : 0.00439 mg/ml ; 0.0000164 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.7

Safety of [ 76283-09-5 ]

Signal Word:Danger Class:8,6.1
Precautionary Statements:P280-P301+P310-P305+P351+P338-P310 UN#:2923
Hazard Statements:H301-H314-H412 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 76283-09-5 ]

* 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 [ 76283-09-5 ]
  • Downstream synthetic route of [ 76283-09-5 ]

[ 76283-09-5 ] Synthesis Path-Upstream   1~15

  • 1
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YieldReaction ConditionsOperation in experiment
89% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 100℃; for 13 h; 4-bromo-1-(bromomethyl)-2-fluorobenzene
NBS (1.07 g, 6.05 mmol) and AIBN (83 mg, 0.50 mmol) were dissolved in CCl4 (10 mL), and 1-bromo-2-fluoro-4-methylbenzene (1 g, 5.04 mmol) was added, followed by heating at 100° C. under reflux for 13 hours.
When the reaction was completed, the reaction mixture was cooled at room temperature, and the generated solid was filtered off, followed by extraction with CCl4 and water two times or more.
The organic layer was treated with sodium sulfate to remove extra water, followed by concentration under reduced pressure, to give 4-bromo-1-(bromomethyl)-2-fluorobenzene (1.2 g, 4.47 mmol) with a yield of 89percent.
1H-NMR (300 MHz, CDCl3) δ 7.51-7.41 (m, 1H), 7.09 (d, J=9.0 Hz, 1H), 6.99 (d, J=8.2 Hz, 1H), 4.34 (s, 2H)
89% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 100℃; for 13 h; [0268] 1-Bromo-2-fluoro-4-methylbenzene (1 g, 5.04 mmol) was added to the solution after dissolving NBS (1.07 g, 6.05 mmol) and AIBN (83 mg, 0.50 mmol) in CCl4 And the mixture was refluxed at 100 deg C for 13 hours. After the reaction was completed, the reaction mixture was cooled at room temperature, and the resulting solid was filtered. After the extraction with CCl4 and water more than 2 times, the organic layer was dried over anhydrous to remove excess water, then concentrated under reduced pressure 4-Bromo-1- (bromomethyl) -2-fluorobenzene (1.2 g, 4.47 mmol) was obtained in 89percent yield
53% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 4 h; Reflux; Inert atmosphere A mixture of 4-bromo-2-fiuoro-l-methylbenzene (available from Aldrich; 2.0 g, 10.58 mmol), N-bromosuccinimide (1.88 g, 10.58 mmol) and AIBN (87 mg, 0.53 mmol) in CCI4 (30 mL) was heated at reflux under nitrogen for 4 h. The reaction mixture was cooled to room temperature, 5percent aqueous Na2S2C"3 solution was added and the mixture was concentrated. Water (10 mL) was added and the mixture was extracted with EtOAc (3 x 50 mL). The combined organic phases were dried (Na2S04), filtered, and evaporated. The residue was purified by chromatography (silica gel, hexane) to give 4-bromo-l-bromomethyl-2-fiuoro-benzene (1.5 g, 53percent) as a colorless liquid.
Reference: [1] Patent: US2015/259350, 2015, A1, . Location in patent: Paragraph 0169; 1070
[2] Patent: KR101745741, 2017, B1, . Location in patent: Paragraph 0268
[3] Patent: WO2014/76104, 2014, A1, . Location in patent: Page/Page column 66
[4] Journal of Medicinal Chemistry, 1995, vol. 38, # 15, p. 2938 - 2945
[5] European Journal of Pharmaceutical Sciences, 2006, vol. 27, # 2-3, p. 188 - 193
[6] Journal of Medicinal Chemistry, 2002, vol. 45, # 16, p. 3406 - 3417
[7] Patent: WO2013/43232, 2013, A2, . Location in patent: Paragraph 00602; 00649
  • 2
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YieldReaction ConditionsOperation in experiment
91% at 100℃; for 0.166667 h; The above compound (7.00 g, 34.1 mmol) was dissolved into 48percent hydrobromic acid (35 mL), and the resultant was caused to react at 100° for 10 minutes. After the end of the reaction, the resultant was neutralized with potassium carbonate. Thereafier, extraction with ethyl acetate was carried out, and this extraction layer was washed with water and a saturated saline solution, then dried over anhydrous magnesium sulfate, and concentrated under a reduced pressure to yield a compound (8.35 g, 91percent). 1H-NMR (CDC13): 4.46 (s, 2H, HnCH2), 7.25-7.29 (m, 3H, Ar).
Reference: [1] Patent: US2017/15684, 2017, A1, . Location in patent: Paragraph 0144; 0145; 0146
  • 3
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Reference: [1] Patent: US2017/15684, 2017, A1,
  • 4
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  • [ 108-59-8 ]
  • [ 134057-95-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2504 - 2520
  • 5
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YieldReaction ConditionsOperation in experiment
100% at 100℃; for 8.5 h; A solution of 4-bromo-2-fluorobenzyl bromide (26.8 g, 100 mmol) and sodium cyanide (5.4 g, 110 mmol) in ethanol (40 ml) and water (10 ml) was stirred at 100°C for 8.5 h. The reaction mixture was cooled to room temperature, then concentrated under reduced pressure, and extracted with ethyl acetate, and the organic layer was washed with saturated sodium chloride solution and dried with anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain the title compound (22.6 g, quant.) as a black oily substance. 1H-NMR (400 Hz, CDCl3) δ: 3.73 (2H, s), 7.27-7.38 (3H, m)
99% at 70℃; for 1 h; To a solution of 4-BROMO-1-BROMOMETHYL-2-FLUORO-BENZENE (8.15 G, 30.4 mmol) dissolved in DMF (16 mL) were added sodium cyanide (2.24 g, 45.6 mmol) and water (2 mL). The reaction was stirred for one hour at 70 C. To the reaction was added 130 mL water; 120 mL saturated NAHC03, and 100 mL EtOAc. The layers were separated, and the aqueous layer was extracted with 3 x 100 mL EtOAc. The combined organics were washed with 100 mL water, and then dried over NA2SO4. After filtering off the solids, the mother liquor was concentrated to the desired product by rotary evaporation (6.5 g, 99percent yield). MS (APCI) : 240 (M+H), 242 (M+2+H).
99% at 60℃; for 12 h; Inert atmosphere To a solution of 4-bromo-l-(bromomethyl)-2-fluorobenzene (500 g, 1.87 mol) in EtOH (2.2 L) stirred under nitrogen at 20 °C was added NaCN (93 g, 1.90 mmol) in one charge. The reaction mixture was stirred at 60 °C for 12 h. Then the solution was concentrated and distributed between DCM (2000 inL) and saturated NaHCC>3 solution (1800 mL). Another batch was repeated using the same procedure. Then the two batches were combined. The combined organic extract was washed with brine, dried over MgS04, filtered and concentrated to provide 2-(4-bromo-2- fluorophenyl)acetonitrile (794 g, 99percent yield): lH NMR (400 MHz, CDC13) δ 7.38-7.27 (m, 3H), 3.72 (s, 2H).
99% at 60℃; for 12 h; Inert atmosphere To a solution of 4-bromo-1-(bromomethyl)-2-fluorobenzene (500 g, 1.87 mol) inEtOH (2.2 L) stirred under N2 at 20 °C was added NaCN (93 g, 1.90 mmol) in one charge. The reaction mixture was stirred at 60 °C for 12 h. Then the solution was concentrated and distributed between DCM (2000 mL) and saturated NaHCO3 solution (1800 mL). Anotherbatch was prepared following the same procedure. Then the two batches were combined. The combined organic extract was washed with brine, dried over Mg504, filtered and concentrated to provide 2-(4-bromo-2-fluorophenyl)acetonitrile (794 g, 99percent): ‘H NIVIR (400 IVIFIz, CDC13) 7.3 8-7.27 (m, 3H), 3.72 (s, 2H).
99% at 1260℃; Inert atmosphere Step 4: 2-(4-Bromo-2-fluorophenyl)acetonitrile To a solution of 4-bromo-l-(bromomethyl)-2-fluorobenzene (500 g, 1.87 mol) in EtOH (2.2 L) stirred under N2 at 20 °C was added NaCN (93 g, 1.90 mmol) in one charge. The reaction mixture was stirred at 60 °C for 12 h. Then the solution was concentrated and distributed between DCM (2000 mL) and saturated NaHC03 solution (1800 mL). Another batch was prepared following the same procedure. Then the two batches were combined. The combined organic extract was washed with brine, dried over MgSO/i, filtered and concentrated to provide 2-(4-bromo- 2-fluorophenyl)acetonitrile (794 g, 99percent): lH NMR (400 MHz, CDC13) δ 7.38-7.27 (m, 3H), 3.72 (s, 2H).
93% for 3 h; Reflux A solution of 4-bromo-1-(bromomethyl)-2-fluorobenzene (1.0 g, 3.73 mmol) in ethanol (5 ml) and water (1 ml) was treated with sodium cyanide (219 mg, 4.48 mmol) and refluxed for 3 hours. The volatiles were evaporated under reduced pressure and the residue was diluted with water and extracted with diethyl ether (.x.2). The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to afford the desired product as a pale yellow solid (0.748 g, 93percent).1H-NMR (400MHz, CDCl3) δ: 7.37-7.26 (3H, m), 3.72 (2H, s); LC/MS Retention time 2.76 mins/M+H not observed C8H579BrFN requires 213.
88% at 26℃; for 10 h; A suspension of NaCN (2.085 g, 42.5 mmol) in DMF (20 mL) was added to a solution of 4-bromo-1-(bromomethyl)-2-fluorobenzene (5.7 g, 21.27 mmol) in DMF (20 mL). The mixture was stirred at 26° C. for 10 h. Then the solution was concentrated and distributed between EA and saturated NaHCO3 solution. The combined organic extract was washed with brine, dried over MgSO4, filtered and concentrated. The resulting 2-(4-bromo-2-fluorophenyl)acetonitrile (4.01 g, 18.74 mmol, 88.0percent yield) was used to next step without further purification. TLC (PE/EA=1/1, Rf 0.5): 1H NMR (400 MHz, CDCl3) δ 7.24-7.37 (m, 3H), 3.70 (s, 2H).
46% at 70℃; for 3 h; To a solution of 4-bromo-1-bromomethyl-2-fluoro-benzene (100g, 373 mmol) in DMF (190 mL) and water (10 mL) was added sodium cyanide (22g, 448 mmol). The reaction was heated to 70 degrees Celsius for 3 hours, concentrated to a volume of 100 mL, and then the solution was diluted with 100 mL of ethyl acetate. After the solids were removed by filtration, water (250 mL) was added and the layers were separated. The organic layer was further washed with 3 x 100 mL of water. The organic layer was dried over MGS04, filtered to remove solids, and then concentrated. Purification by distillation gave the desired product (37.124g, 46percent). B. P. = 72-75 degrees Celsius.

Reference: [1] Patent: EP2700643, 2014, A1, . Location in patent: Paragraph 0188
[2] Patent: WO2004/74270, 2004, A2, . Location in patent: Page 111-112
[3] Patent: WO2014/141187, 2014, A1, . Location in patent: Page/Page column 54; 44; 56; 57
[4] Patent: WO2016/38519, 2016, A1, . Location in patent: Page/Page column 36
[5] Patent: WO2016/38552, 2016, A1, . Location in patent: Page/Page column 50
[6] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 7, p. 623 - 628
[7] Patent: US2010/137276, 2010, A1, . Location in patent: Page/Page column 23
[8] Patent: US2014/275111, 2014, A1, . Location in patent: Paragraph 0233; 0234
[9] Organic Process Research and Development, 2006, vol. 10, # 4, p. 814 - 821
[10] Patent: WO2004/74270, 2004, A2, . Location in patent: Page 237
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YieldReaction ConditionsOperation in experiment
94% at 60℃; for 2 h; Potassium cyanide (1.3 g, 20 mmol) was added to a mixed solution of 4-bromo-2-fluorobenzyl bromide (5.00 g, 18.7 mmol) in ethanol-water (3:1, 40 ml), and the mixture was stirred at 60°C for 2 hours. The reaction mixture was poured into water and, after the mixture was extracted with ethyl acetate, the organic layer was washed with saturated aqueous NaCl solution, and dried over anhydrous sodium sulfate. The residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (elution solvent: n-hexane/ethyl acetate) to obtain to obtain (4-bromo-2-fluorophenyl)acetonitrile as a colorless solid (3.75 g, yield: 94percent). 1H-NMR (400MHz, CDCl3) δ 7.35-7.26 (3H, m) , 3.72 (2H, s).
87% at 40℃; for 3 h; To a solution of 4-bromo-1-(bromomethyl)-2-fluorobenzene (5.0 g, 18.7 mmol) in DMF (80 mL) and H2O (8 mL) was added KCN (1.21 g, 18.7 mmol). The mixture was heated to 40° C. for 3 hours before it was cooled down to room temperature. The reaction was diluted with H2O (40 mL) and extracted with Et2O (3.x.100 mL). The combined organic layers were washed with brine and dried over Na2SO4. The solvent was removed and the residue was purified by flash column chromatography (0-15percent EtOAc in hexanes) to give the product (3.5 g, 87percent yield). 1H NMR (300 MHz, CDCl3) δ: 3.72 (s, 2H), 7.26-7.35 (m, 3H).
Reference: [1] Patent: WO2006/46593, 2006, A1, . Location in patent: Page/Page column 177
[2] Patent: EP1764075, 2007, A1, . Location in patent: Page/Page column 104
[3] Patent: WO2006/109633, 2006, A1, . Location in patent: Page/Page column 165
[4] Patent: US2005/176701, 2005, A1, . Location in patent: Page/Page column 58
[5] Patent: US2006/160800, 2006, A1, . Location in patent: Page/Page column 76
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YieldReaction ConditionsOperation in experiment
99% at 70℃; for 1 h; To a solution of 4-bromo-1~bromomethyl-2-fluoro-benzene (8.15 g, 30.4 mmol) dissolved in DMF (16 mL) were added sodium cyanide (2.24 g, 45.6 mmol) and water (2 ml_). The reaction was stirred for one hour at 70 °C. To the reaction was added 130 ml water; 120 ml saturated NaHCO3, and 100 mL EtOAc. The layers were separated, and the aqueous layer was extracted with 3 x 100 mL EtOAc. The combined organics were washed with 100 mL water, and then dried over Na2SO4. After filtering off the solids, the mother liquor was concentrated to the desired product by rotary evaporation (6.5 g, 99percent yield). MS (APCI): 240 (M+H), 242 (M+2+H).
96% at 20℃; for 4 h; Preparation of (4-Bromo-2-fluoro-phenyl)-acetonitrile
Sodium cyanide (1.37 g, 28.00 mmol) was added to a stirred solution of 2-fluoro-4-bromo benzyl bromide (5.0 g, 18.66 mmol) in dry DMSO (60 mL) at ambient temperature under nitrogen.
The reaction was stirred for 4 h at ambient temperature then poured into H2O (150 mL) and extracted with EtOAc.
The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo to give the intermediate title compound as a brown oil (3.85 g, 96percent).
Electrospray mass spectrum: M=213, M+2=215
46% at 70℃; for 3 h; To a solution of 4-bromo-1-bromomethyl-2-fluoro-benzene (10 g, 373 mmol) in DMF (190 mL) and water (10 mL) was added sodium cyanide (2 g, 448 mmol). The reaction was heated to 70 degrees Celsius for 3 hours, concentrated to a volume of 100 mL, and then the solution was diluted with 100 mL of ethyl acetate. After the solids were removed by filtration, water (250 mL) was added and the layers were separated. The organic layer was further washed with 3.x.100 mL of water. The organic layer was dried over MgSO4, filtered to remove solids, and then concentrated. Purification by distillation gave the desired product (37.12 g, 46percent). B.P.=72-75 degrees Celsius.
Reference: [1] Patent: WO2006/18725, 2006, A1, . Location in patent: Page/Page column 172
[2] Patent: US7034045, 2006, B1, . Location in patent: Page/Page column 84-85
[3] Patent: US2005/176701, 2005, A1, . Location in patent: Page/Page column 111
[4] Journal of Medicinal Chemistry, 2007, vol. 50, # 17, p. 3969 - 3972
  • 8
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YieldReaction ConditionsOperation in experiment
87% at 20 - 40℃; for 3 h; To a solution OF 4-BROMO-1-(BROMOMETHYL)-2-FLUOROBENZENE (5.0 g, 18.7 mmol) in DMF (80 mL) and H20 (8 mL) was added KCN (1.21 g, 18.7 mmol). The mixture was heated to 40 C for 3 hours before it was cooled down to room temperature. The reaction was diluted with H20 (40 mL) and extracted with ET20 (3 x 100 mL). The combined organic layers were washed with brine and dried over NA2SO4. The solvent was removed and the residue was purified by flash column chromatography (0-15percent EtOAc in hexanes) to give the product (3.5 g, 87percent YIELD). H NMR (300 MHz, CDC13) 5 : 3.72 (s, 2 H), 7. 26-7.35 (m, 3 H).
7 g With tetrabutylammomium bromide In dichloromethane; water at 20℃; for 15 h; To a solution of 4-bromo- l -(bromomethyl)-2-fluorobenzene (9 g, crude) in DCM (50 mL) and H20 (50 mL) was added CN (6.56 g, 100.74 mmol) and TBAB (1 g) and stirred at r.t. for 15 h. The mixture was washed with water, extracted with DCM (2 x 50 mL). The combined layers were washed with brine (100 mL), dried over Na2SC>4 and concentrated to afford 75c (7 g) which was used in the next step without further purification. LCMS m/z 214 (M+l)+.
Reference: [1] Patent: WO2004/74270, 2004, A2, . Location in patent: Page 130
[2] Patent: WO2013/43232, 2013, A2, . Location in patent: Paragraph 00603; 00650
[3] Patent: WO2013/40863, 2013, A1, . Location in patent: Page/Page column 100
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YieldReaction ConditionsOperation in experiment
84% With potassium cyanide In ethanol; water; ethyl acetate REFERENCE EXAMPLE 60
(4-Bromo-2-fluorophenyl)acetonitrile
To a solution of 4-bromo-2-fluorobenzylbromide (44.5 g, 166 mmol) in EtOH (118 mL) was added KCN (13.13 g, 182 mmol) and the mixture was stirred at reflux under an argon atmosphere for 18 h.
The mixture was allowed to cool and the solvent was concentrated.
The residue thus obtained was dissolved in a mixture of EtOAc and H2 O and the two phases were separated.
The aqueous phase was extracted with EtOAc and the combined organic phases dried and concentrated to a crude product.
Purification by chromatography on silica gel (hexane-EtOAc, 10percent) afforded the title compound as a reddish oil (30.0 g, 84percent).
1 H-NMR-(CDCl3) δ (TMS): 3.71 (s 2H), 7.30 (m, 3H).
60% With potassium cyanide In ethanol Step (1)
Preparation of 4-Bromo-2-fluorophenylacetonitrile
KCN (2.91 g, 44.8 mmol) was added to a solution of 4-bromo-2-fluorobenzyl bromide (10.0 g, 37.3 mmol) in absolute ethanol (150 mL), and the resulting mixture heated to reflux for 18 hours.
The mixture was cooled to room temperature and partitioned between water (100 mL) and ether (250 mL).
The layers were separated and the aqueous layer reextracted with ether (150 mL).
The combined organic layers were washed with water, brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give a light yellow oil.
The oil was triturated with hexanes to give a white crystalline solid which was collected by filtration and dried in vacuo (3.93 g).
The filtrate was concentrated and the residue purified by chromatography on silica gel with elution by EtOAc/hexanes (5:95) to give additional product (0.9 g).
The solids were combined to give the desired product (total 4.83 g, 60percent) of sufficient purity for use in the subsequent reaction.
NMR (DMSO-d6): δ 7.63 (dd, J1 =9.2 Hz, J2 =1.3 Hz, 1H), 7.42 (m, 2H).
4.05 (s, 2H).
Reference: [1] Patent: US2004/63680, 2004, A1,
[2] Patent: US5827863, 1998, A,
[3] Patent: US4895862, 1990, A,
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YieldReaction ConditionsOperation in experiment
53% at 20℃; for 19.5 h; (1)
Production of (4-bromo-2-fluorophenyl)acetonitrile:
Tetraethylammonium cyanide (3.8 g, 24.3 mmol) was added to a DMF solution (50 mL) of 4-bromo-1-(bromomethyl)-2-fluorobenzene (5.0 g, 18.7 mmol), and stirred at room temperature for 19.5 hours.
Next, aqueous saturated ammonium chloride solution was added to the reaction liquid, and extracted with ethyl acetate.
The obtained organic layer was washed with saturated saline, then dried with anhydrous sodium sulfate, and filtered.
The obtained filtrate was concentrated under reduced pressure, then the residue was purified by silica gel column chromatography (hexane:ethyl acetate = 10:0 to 9:1) to obtain the entitled compound (2.11 g, 53 percent).
Mass Spectrum (APCI): 214.0 (M+H).
Reference: [1] Patent: EP1916239, 2008, A1, . Location in patent: Page/Page column 33
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Reference: [1] Patent: WO2013/28447, 2013, A1, . Location in patent: Page/Page column 93
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  • [ 114897-91-5 ]
Reference: [1] Patent: EP1806332, 2007, A1,
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  • [ 114897-92-6 ]
Reference: [1] Patent: US2014/275111, 2014, A1,
[2] Patent: WO2014/141187, 2014, A1,
[3] Patent: WO2016/38519, 2016, A1,
[4] Patent: WO2016/38552, 2016, A1,
[5] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 7, p. 623 - 628
  • 14
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  • [ 193290-19-6 ]
Reference: [1] Patent: EP1806332, 2007, A1,
[2] Patent: WO2013/43232, 2013, A2,
[3] Patent: WO2014/141187, 2014, A1,
[4] Patent: WO2016/38519, 2016, A1,
[5] Patent: WO2016/38552, 2016, A1,
[6] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 7, p. 623 - 628
[7] Patent: WO2013/28447, 2013, A1,
[8] Patent: WO2013/28447, 2013, A1,
[9] Patent: WO2006/109633, 2006, A1,
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Reference: [1] Patent: EP2700643, 2014, A1,
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4-Bromo-1-fluoro-2-methylbenzene

Similarity: 0.88

Aryls

Chemical Structure| 162744-60-7

[ 162744-60-7 ]

5-Bromo-2-(bromomethyl)-1,3-difluorobenzene

Similarity: 0.93

Chemical Structure| 52548-00-2

[ 52548-00-2 ]

1-Bromo-4-fluoro-2,3-dimethylbenzene

Similarity: 0.91

Chemical Structure| 51436-99-8

[ 51436-99-8 ]

4-Bromo-2-fluorotoluene

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Chemical Structure| 216755-57-6

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1-Bromo-3-(bromomethyl)-5-fluorobenzene

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Chemical Structure| 51437-00-4

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4-Bromo-1-fluoro-2-methylbenzene

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Bromides

Chemical Structure| 162744-60-7

[ 162744-60-7 ]

5-Bromo-2-(bromomethyl)-1,3-difluorobenzene

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Chemical Structure| 52548-00-2

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1-Bromo-4-fluoro-2,3-dimethylbenzene

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Chemical Structure| 51436-99-8

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4-Bromo-2-fluorotoluene

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Chemical Structure| 216755-57-6

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1-Bromo-3-(bromomethyl)-5-fluorobenzene

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Chemical Structure| 51437-00-4

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4-Bromo-1-fluoro-2-methylbenzene

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Benzyl bromides

Chemical Structure| 162744-60-7

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5-Bromo-2-(bromomethyl)-1,3-difluorobenzene

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Chemical Structure| 216755-57-6

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1-Bromo-3-(bromomethyl)-5-fluorobenzene

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Chemical Structure| 61150-57-0

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2-Bromo-4-fluorobenzylbromide

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Chemical Structure| 149947-16-0

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1-Bromo-3-(bromomethyl)-2-fluorobenzene

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Chemical Structure| 446-48-0

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1-(Bromomethyl)-2-fluorobenzene

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