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Chemistry
Organic Building Blocks
Bromides
1,3-Bis(3,bromopropyl)benzene
Chemistry
Organic Building Blocks
Bromides
Benzene Compounds

[ CAS No. 41009-86-3 ]

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Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 41009-86-3
Chemical Structure| 41009-86-3
Chemical Structure| 41009-86-3
Structure of 41009-86-3 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 41009-86-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 41009-86-3 ]

SDS Specification
Alternatived Products of [ 41009-86-3 ]

Product Details of [ 41009-86-3 ]

CAS No. :41009-86-3 MDL No. :MFCD31555404
Formula : C12H16Br2 Boiling Point : -
Linear Structure Formula :- InChI Key :MVJDECNMMQGXKW-UHFFFAOYSA-N
M.W :320.06 Pubchem ID :54072282
Synonyms :

Calculated chemistry of [ 41009-86-3 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 6
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 71.34
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.35
Log Po/w (XLOGP3) : 5.73
Log Po/w (WLOGP) : 4.34
Log Po/w (MLOGP) : 4.93
Log Po/w (SILICOS-IT) : 5.27
Consensus Log Po/w : 4.72

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.36
Solubility : 0.00141 mg/ml ; 0.00000441 mol/l
Class : Moderately soluble
Log S (Ali) : -5.5
Solubility : 0.00102 mg/ml ; 0.00000318 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.51
Solubility : 0.0000991 mg/ml ; 0.00000031 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.78

Safety of [ 41009-86-3 ]

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 [ 41009-86-3 ]

* 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.

  • Downstream synthetic route of [ 41009-86-3 ]

[ 41009-86-3 ] Synthesis Path-Downstream   1~30

  • 1
  • [ 41009-85-2 ]
  • [ 41009-86-3 ]
YieldReaction ConditionsOperation in experiment
80% With dibromotriphenylphosphorane In dichloromethane at 20℃; for 24h; 5.D Step D To a stirred solution of the intermediate from Step C (2.5 g, 12.8 mmol) was added dibromotriphenylphosphorane (21.7 g, 51.5 mmol) in DCM (200 mL). The resulting mixture was stirred at ambient temperature overnight (24 hours) and then the mixture was concentrated under reduced pressure and hexane (200 mL) was added to the residue. The heterogeneous mixture was stirred rapidly for 30 minutes and then the hexane layer was decanted from the insoluble material. The organic layer was washed with water (2×100 mL), saturated NaCl (1×100 mL), dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to afford 3.14 g of the title intermediate (80% yield), which was used without further purification.
With hydrogen bromide
With sulfuric acid; sodium bromide
Reference： [1]Current Patent Assignee: THERAVANCE BIOPHARMA, INC. - US2005/203167, 2005, A1 Location in patent: Page/Page column 21
[2]Effenberger,F.; Kurtz,W. [Chemische Berichte, 1973, vol. 106, p. 511 - 524] Ruzicka; Buijs; Stoll [Helvetica Chimica Acta, 1932, vol. 15, p. 1220,1224]
[3]Schimelpfenig,C.W. [Journal of Organic Chemistry, 1975, vol. 40, p. 1493 - 1494]
  • 2
  • [ 41009-86-3 ]
  • [ 105-53-3 ]
  • 5,5'-<i>m</i>-phenylene-di-valeric acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Reaktion ueber mehrere Stufen;
Reference： [1]Ruzicka; Buijs; Stoll [Helvetica Chimica Acta, 1932, vol. 15, p. 1220,1224]
  • 3
  • [ 41009-86-3 ]
  • [ 151-50-8 ]
  • [ 54698-76-9 ]
Reference： [1]Schimelpfenig,C.W. [Journal of Organic Chemistry, 1975, vol. 40, p. 1493 - 1494]
  • 4
  • [ 41009-86-3 ]
  • [ 35896-11-8 ]
YieldReaction ConditionsOperation in experiment
(i) NBS, (PhCO)2O2, AIBN, (ii) Zn-Cu; Multistep reaction;
Reference： [1]Effenberger,F.; Kurtz,W. [Chemische Berichte, 1973, vol. 106, p. 511 - 524]
  • 5
  • [ 41009-86-3 ]
  • [ 105-53-3 ]
  • [ 54698-70-3 ]
YieldReaction ConditionsOperation in experiment
(i) NaOEt, (ii) aq. HCl, (iii) (esterification); Multistep reaction;
Reference： [1]Schimelpfenig,C.W. [Journal of Organic Chemistry, 1975, vol. 40, p. 1493 - 1494]
  • 6
  • [ 41009-86-3 ]
  • [ 603-35-0 ]
  • [ 87603-85-8 ]
YieldReaction ConditionsOperation in experiment
89% In methyl cyclohexane at 110 - 115℃; for 160h;
Reference： [1]Zipplies, Matthias F.; Krieger, Claus; Staab, Heinz A. [Tetrahedron Letters, 1983, vol. 24, # 18, p. 1925 - 1928]
  • 7
  • [ 41009-86-3 ]
  • [ 603-35-0 ]
  • [ 87603-85-8 ]
  • C48H46P2(2+)*2Br(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% In methyl cyclohexane; benzene at 110 - 115℃; for 160h;
Reference： [1]Staab, Heinz A.; Zipplies, Matthias F.; Mueller, Thomas; Storch, Matthias; Krieger, Claus [Chemische Berichte, 1994, vol. 127, # 9, p. 1667 - 1680]
YieldReaction ConditionsOperation in experiment
Rk.mit KCN;
Rk.mit Malonester;
  • 9
  • [ 41009-86-3 ]
  • [ 87603-91-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 63 percent / benzene; methylcyclohexane / 160 h / 110 - 115 °C 2: 1.) potassium tert-butylate / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 90 min; warming up to r.t. within 1 h; r.t., 2 h 3: 85 percent / 2.5percent NaOH/H2O, (n-Bu)4NBr / toluene / 38 h / Heating 4: 79 percent / KOH / ethanol; H2O / 1.17 h / 85 - 90 °C 5: H2, boric acid / 10percent Pd/C / acetic acid / 20 °C / 760 Torr
Multi-step reaction with 5 steps 1: 89 percent / methylcyclohexane / 160 h / 110 - 115 °C 2: t-BuOK / tetrahydrofuran / -78 °C 3: 85 percent / NaOH / 4N>Cl phase-transfer catalysis / toluene; H2O 4: 79 percent / KOH / ethanol; H2O 5: 4 eq. H2 / Pd/C / acetic acid / 20 °C
Reference： [1]Staab, Heinz A.; Zipplies, Matthias F.; Mueller, Thomas; Storch, Matthias; Krieger, Claus [Chemische Berichte, 1994, vol. 127, # 9, p. 1667 - 1680]
[2]Zipplies, Matthias F.; Krieger, Claus; Staab, Heinz A. [Tetrahedron Letters, 1983, vol. 24, # 18, p. 1925 - 1928]
  • 10
  • [ 41009-86-3 ]
  • [ 87603-90-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 63 percent / benzene; methylcyclohexane / 160 h / 110 - 115 °C 2: 1.) potassium tert-butylate / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 90 min; warming up to r.t. within 1 h; r.t., 2 h 3: 85 percent / 2.5percent NaOH/H2O, (n-Bu)4NBr / toluene / 38 h / Heating 4: 79 percent / KOH / ethanol; H2O / 1.17 h / 85 - 90 °C
Multi-step reaction with 4 steps 1: 89 percent / methylcyclohexane / 160 h / 110 - 115 °C 2: t-BuOK / tetrahydrofuran / -78 °C 3: 85 percent / NaOH / 4N>Cl phase-transfer catalysis / toluene; H2O 4: 79 percent / KOH / ethanol; H2O
Reference： [1]Staab, Heinz A.; Zipplies, Matthias F.; Mueller, Thomas; Storch, Matthias; Krieger, Claus [Chemische Berichte, 1994, vol. 127, # 9, p. 1667 - 1680]
[2]Zipplies, Matthias F.; Krieger, Claus; Staab, Heinz A. [Tetrahedron Letters, 1983, vol. 24, # 18, p. 1925 - 1928]
  • 11
  • [ 41009-86-3 ]
  • [ 87603-89-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 63 percent / benzene; methylcyclohexane / 160 h / 110 - 115 °C 2: 1.) potassium tert-butylate / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 90 min; warming up to r.t. within 1 h; r.t., 2 h 3: 85 percent / 2.5percent NaOH/H2O, (n-Bu)4NBr / toluene / 38 h / Heating
Multi-step reaction with 3 steps 1: 89 percent / methylcyclohexane / 160 h / 110 - 115 °C 2: t-BuOK / tetrahydrofuran / -78 °C 3: 85 percent / NaOH / 4N>Cl phase-transfer catalysis / toluene; H2O
Reference： [1]Staab, Heinz A.; Zipplies, Matthias F.; Mueller, Thomas; Storch, Matthias; Krieger, Claus [Chemische Berichte, 1994, vol. 127, # 9, p. 1667 - 1680]
[2]Zipplies, Matthias F.; Krieger, Claus; Staab, Heinz A. [Tetrahedron Letters, 1983, vol. 24, # 18, p. 1925 - 1928]
  • 12
  • [ 41009-86-3 ]
  • [ 87603-92-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 63 percent / benzene; methylcyclohexane / 160 h / 110 - 115 °C 2: 1.) potassium tert-butylate / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 90 min; warming up to r.t. within 1 h; r.t., 2 h 3: 85 percent / 2.5percent NaOH/H2O, (n-Bu)4NBr / toluene / 38 h / Heating 4: 79 percent / KOH / ethanol; H2O / 1.17 h / 85 - 90 °C 5: H2, boric acid / 10percent Pd/C / acetic acid / 20 °C / 760 Torr 6: boric acid / acetic acid; acetic acid / 14 h / 55 - 60 °C
Multi-step reaction with 6 steps 1: 89 percent / methylcyclohexane / 160 h / 110 - 115 °C 2: t-BuOK / tetrahydrofuran / -78 °C 3: 85 percent / NaOH / 4N>Cl phase-transfer catalysis / toluene; H2O 4: 79 percent / KOH / ethanol; H2O 5: 4 eq. H2 / Pd/C / acetic acid / 20 °C 6: AcOH, B(OH)3 / 12 h / 60 °C / flavin synthesis of Cuhn and Weygand
Reference： [1]Staab, Heinz A.; Zipplies, Matthias F.; Mueller, Thomas; Storch, Matthias; Krieger, Claus [Chemische Berichte, 1994, vol. 127, # 9, p. 1667 - 1680]
[2]Zipplies, Matthias F.; Krieger, Claus; Staab, Heinz A. [Tetrahedron Letters, 1983, vol. 24, # 18, p. 1925 - 1928]
  • 13
  • [ 41009-86-3 ]
  • [ 87603-88-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 63 percent / benzene; methylcyclohexane / 160 h / 110 - 115 °C 2: 1.) potassium tert-butylate / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 90 min; warming up to r.t. within 1 h; r.t., 2 h
Multi-step reaction with 2 steps 1: 89 percent / methylcyclohexane / 160 h / 110 - 115 °C 2: t-BuOK / tetrahydrofuran / -78 °C
Reference： [1]Staab, Heinz A.; Zipplies, Matthias F.; Mueller, Thomas; Storch, Matthias; Krieger, Claus [Chemische Berichte, 1994, vol. 127, # 9, p. 1667 - 1680]
[2]Zipplies, Matthias F.; Krieger, Claus; Staab, Heinz A. [Tetrahedron Letters, 1983, vol. 24, # 18, p. 1925 - 1928]
  • 14
  • [ 41009-86-3 ]
  • [ 87603-87-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 63 percent / benzene; methylcyclohexane / 160 h / 110 - 115 °C 2: 1.) potassium tert-butylate / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 90 min; warming up to r.t. within 1 h; r.t., 2 h
Multi-step reaction with 2 steps 1: 89 percent / methylcyclohexane / 160 h / 110 - 115 °C 2: t-BuOK / tetrahydrofuran / -78 °C
Reference： [1]Staab, Heinz A.; Zipplies, Matthias F.; Mueller, Thomas; Storch, Matthias; Krieger, Claus [Chemische Berichte, 1994, vol. 127, # 9, p. 1667 - 1680]
[2]Zipplies, Matthias F.; Krieger, Claus; Staab, Heinz A. [Tetrahedron Letters, 1983, vol. 24, # 18, p. 1925 - 1928]
  • 15
  • [ 41009-86-3 ]
  • 1-acetyl-20-amino-1-aza<4.4>metacyclophane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 63 percent / benzene; methylcyclohexane / 160 h / 110 - 115 °C 2: 1.) potassium tert-butylate / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 90 min; warming up to r.t. within 1 h; r.t., 2 h 3: 85 percent / 2.5percent NaOH/H2O, (n-Bu)4NBr / toluene / 38 h / Heating 4: 76 percent / H2 / 10percent Pd/C / ethanol; acetic acid / 2 h / 20 °C / 760 Torr
Reference： [1]Staab, Heinz A.; Zipplies, Matthias F.; Mueller, Thomas; Storch, Matthias; Krieger, Claus [Chemische Berichte, 1994, vol. 127, # 9, p. 1667 - 1680]
  • 16
  • [ 41009-86-3 ]
  • [ 960604-33-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Reaktion ueber mehrere Stufen 2: ethanol; sodium
Reference： [1]Ruzicka; Buijs; Stoll [Helvetica Chimica Acta, 1932, vol. 15, p. 1220,1224]
  • 17
  • [ 10133-62-7 ]
  • [ 41009-86-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanol; sodium 2: HBr
Reference： [1]Ruzicka; Buijs; Stoll [Helvetica Chimica Acta, 1932, vol. 15, p. 1220,1224]
  • 18
  • [ 626-19-7 ]
  • [ 41009-86-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: (i) Py, (ii) (decarboxylation) 2: H2, aq. NaOH / Pd-C 3: (i) SOCl2, (ii) /BRN= 1098229/ 4: LiAlH4 / diethyl ether 5: NaBr, aq. H2SO4
Reference： [1]Schimelpfenig,C.W. [Journal of Organic Chemistry, 1975, vol. 40, p. 1493 - 1494]
  • 19
  • [ 37710-81-9 ]
  • [ 41009-86-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: H2, aq. NaOH / Pd-C 2: (i) SOCl2, (ii) /BRN= 1098229/ 3: LiAlH4 / diethyl ether 4: NaBr, aq. H2SO4
Reference： [1]Schimelpfenig,C.W. [Journal of Organic Chemistry, 1975, vol. 40, p. 1493 - 1494]
  • 20
  • [ 6221-61-0 ]
  • [ 41009-86-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: LiAlH4 / diethyl ether 2: NaBr, aq. H2SO4
Multi-step reaction with 2 steps 1: LiAlH4 2: HBr
Reference： [1]Schimelpfenig,C.W. [Journal of Organic Chemistry, 1975, vol. 40, p. 1493 - 1494]
[2]Effenberger,F.; Kurtz,W. [Chemische Berichte, 1973, vol. 106, p. 511 - 524]
  • 21
  • [ 41009-86-3 ]
  • [ 54698-71-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (i) NaOEt, (ii) aq. HCl, (iii) (esterification) 2: (i) KOtBu, xylene, (ii) (saponification), (iii) acid
Reference： [1]Schimelpfenig,C.W. [Journal of Organic Chemistry, 1975, vol. 40, p. 1493 - 1494]
  • 22
  • [ 41009-86-3 ]
  • [ 54698-75-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 2: (hydrolysis)
Reference： [1]Schimelpfenig,C.W. [Journal of Organic Chemistry, 1975, vol. 40, p. 1493 - 1494]
  • 23
  • [ 41009-86-3 ]
  • [ 54698-77-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (i) NaOEt, (ii) aq. HCl, (iii) (esterification) 2: (saponification)
Reference： [1]Schimelpfenig,C.W. [Journal of Organic Chemistry, 1975, vol. 40, p. 1493 - 1494]
  • 24
  • [ 41009-86-3 ]
  • [ 54698-69-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 2: (hydrolysis) 3: (esterification)
Reference： [1]Schimelpfenig,C.W. [Journal of Organic Chemistry, 1975, vol. 40, p. 1493 - 1494]
  • 25
  • [ 41009-86-3 ]
  • 4,17-Dioxo<7.7>metacyclophan [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 2: (hydrolysis) 3: (esterification) 4: (i) KOtBu, xylene, (ii) (saponification), (iii) acid
Reference： [1]Schimelpfenig,C.W. [Journal of Organic Chemistry, 1975, vol. 40, p. 1493 - 1494]
  • 26
  • [ 41009-86-3 ]
  • [ 54738-98-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (i) NaOEt, (ii) aq. HCl, (iii) (esterification) 2: (i) KOtBu, xylene, (ii) (saponification), (iii) acid
Reference： [1]Schimelpfenig,C.W. [Journal of Organic Chemistry, 1975, vol. 40, p. 1493 - 1494]
  • 27
  • [ 6082-86-6 ]
  • [ 41009-86-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (i) SOCl2, (ii) /BRN= 1098229/ 2: LiAlH4 / diethyl ether 3: NaBr, aq. H2SO4
Multi-step reaction with 3 steps 1: H2SO4 2: LiAlH4 3: HBr
Reference： [1]Schimelpfenig,C.W. [Journal of Organic Chemistry, 1975, vol. 40, p. 1493 - 1494]
[2]Effenberger,F.; Kurtz,W. [Chemische Berichte, 1973, vol. 106, p. 511 - 524]
  • 28
  • [ 41009-86-3 ]
  • [ 76-05-1 ]
  • 2-((S)-1-{3-[3-(3-methylaminopropyl)phenyl]propyl}pyrrolidin-3-yl)-2,2-diphenylacetamide bis(trifluoroacetate) salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% Stage #1: 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide; 1,3-bis(3-bromopropyl)benzene With potassium carbonate In acetonitrile at 20℃; for 18h; Stage #2: methylamine In tetrahydrofuran; acetonitrile at 20℃; for 18h; Stage #3: trifluoroacetic acid 5.E Step E To a flask was added 2,2-diphenyl-2-(S)-pyrrolidin-3-ylacetamide (880 mg, 1.57 mmol), the intermediate from Step D (1.0 g, 1.57 mmol), ACN (2 mL) and potassium carbonate (1.4 g, 4.7 mmol) and the resulting mixture was stirred overnight (18 hours) at ambient temperature. Methylamine (2.0 M in THF, 7.8 mL, 15.7 mmol) was added and the resulting mixture was stirred at ambient temperature overnight (18 hours). The reaction mixture was concentrated under reduced pressure and a solution of 1:1 acetic acid/water (1.0 mL) was added to the residue. This mixture was chromatographed on reverse phase silica gel (gradient elution, 10-50% ACN/water) to afford 303 mg of the title compound (27% yield) as a bis(trifluoroacetate) salt. MS m/z: [M+H+] calc'd for C31H39N3O 470.3; found 470.6. Retention time=2.61 min (10-70% ACN: H2O, reverse phase HPLC).
Reference： [1]Current Patent Assignee: THERAVANCE BIOPHARMA, INC. - US2005/203167, 2005, A1 Location in patent: Page/Page column 21
  • 29
  • [ 41009-86-3 ]
  • 5,5'-(1,3-phenylene)bis(2,2-dimethylpentanoic acid) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 1 h / -78 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: water; potassium hydroxide / ethanol / 4 h / Reflux
Reference： [1]Current Patent Assignee: ESPERVITA THERAPEUTICS - US2021/24447, 2021, A1
  • 30
  • [ 41009-86-3 ]
  • [ 97-62-1 ]
  • diethyl 5,5'-(1,3-phenylene)bis(2,2-dimethylpentanoate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% Stage #1: Ethyl isobutyrate With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 1h; Inert atmosphere; Stage #2: 1,3-bis(3-bromopropyl)benzene With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone In tetrahydrofuran; n-heptane; ethylbenzene at 20℃; Inert atmosphere; 12 Dimethyl m-benzene-bis(2,2-dimethyl)pentanoate (D2) Under Ar-atmosphere, to a solution of ethyl isobutyrate (21.2 g, 24.4 mL, 183 mmol) in anhydrous THF (200 mL) was added dropwise lithium diisopropylamide (2.0 M in heptane/THF/ethylbenzene, 91.5 mL, 183 mmol) at -78° C. After 1 h, a solution of m-bis(3-bromopropyl)benzene (D1) (prepared according to Schimelpfenig, C. W. J. Org. Chem. 1975, 40, 1493-1494 and Effenberger, F.; Kurtz, W. Chem. Ber. 1973, 106, 511-524; 26.6 g, 83.1 mmol) in anhydrous THF (50 mL) was added dropwise, followed by the addition of DMPU (25 mL). The reaction mixture was allowed to warm to room temperature overnight, then cooled with an ice-bath, and hydrolyzed with saturated NH4Cl solution (100 mL). Deionized water (100 mL) was added and the layers were separated. The aqueous layer was extracted with ethyl acetate (3*100 mL). The combined organic layers were washed with saturated NaCl solution (100 mL), 1 N hydrochloric acid (2*100 mL), saturated NaHCO3 solution (100 mL), and saturated NaCl solution (100 mL). The combined organic phases were dried over MgSO4, concentrated in vacuo, and dried in high vacuo. The residue was purified by flash chromatography on silica (hexanes/ethyl acetate=95/5) to give diethyl 5,5'-(1,3-phenylene)bis(2,2-dimethylpentanoate) (15.7 g, 48%) as a yellowish oil. 1H NMR (CDCl3): δ=7.17 (t, 1 H, J=7.0 Hz), 6.97 (m, 3 H), 4.09 (q, 4 H, J=7.3 Hz), 2.55 (m, 4 H), 1.56 (m, 8 H), 1.22 (t, 6 H, J=7.3 Hz), 1.15 (s, 12 H). 13C NMR (CDCl3): δ=178.02, 142.37, 128.58, 128.32, 125.86, 60.31, 42.25, 40.52, 36.48, 27.03, 25.30, 14.39.
Reference： [1]Current Patent Assignee: ESPERVITA THERAPEUTICS - US2021/24447, 2021, A1 Location in patent: Paragraph 0561-0563

Tags: 41009-86-3 synthesis path| 41009-86-3 SDS| 41009-86-3 COA| 41009-86-3 purity| 41009-86-3 application| 41009-86-3 NMR| 41009-86-3 COA| 41009-86-3 structure

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