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Chemical Structure| 3945-85-5

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Product Details of [ 3945-85-5 ]

CAS No. :3945-85-5
Formula : C11H15BrO2
M.W : 259.14
SMILES Code : COC1=CC(CCCBr)=CC=C1OC

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Application In Synthesis of [ 3945-85-5 ]

* 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.

  • Downstream synthetic route of [ 3945-85-5 ]

[ 3945-85-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 3929-47-3 ]
  • [ 3945-85-5 ]
YieldReaction ConditionsOperation in experiment
99% With N-Bromosuccinimide; triphenylphosphine; In dichloromethane; at 0℃; for 1h; Triphenylphosphine (802 mg, 3.06mmol) and N-bromosuccinimide (544 mg, 3.06 mmol) were added to a solution of 3-(3,4-Dimethoxyphenyl)-1-propanol (500 mg, 2.55 mmol) in CH2Cl2 (10 mL) at 0 C under nitrogenatmosphere. The reaction mixture was stirred at 0 C for 1 h. The reaction was quenched with saturated aqueous solution of NaHCO3 (10 mL) and extracted from theaqueous phase with MC (10 mL x 3). The organic layer was dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by flash column chromatography(40% EtOAc/hexane) to yield 655 mg (2.53 mmol, 99%) of 4-(3-bromopropyl)-1,2-dimethoxybenzene as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 2.06-2.13 (m, 2H),2.68 (t, J = 7.3 Hz, 2H), 3.34 (t, J = 6.5 Hz, 2H), 3.81 (s, 3H), 3.83 (s, 3H), 6.69-6.71 (m, 2H),6.76 (d, J = 8.5 Hz, 1H); 13C NMR(100 MHz, CDCl3) δ 33.03, 33.36, 34.17, 55.69, 55.76, 111.23,111.74, 120.27, 132.93, 147.29, 148.78; MS (EI) 258 (M+), 260 (M+), 151 (100); HRMS (EI) calcdfor C11H1579BrO2 (M+) 258.0255, found 258.0254.
87% With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0℃; for 2h; After 3 (7.60 g, 38.73 mmol) was dissolved in dichloromethane (DCM) (50 mL), along with CBr4 (13.50 g, 40.67 mmol), the reaction mixture was cooled to 0C, and PPh3 (10.68 g, 40.67 mmol) was added slowly. The resultant reaction solution was stirred for 2 h,and the reaction solvents were removed under reduced pressure. The residue was purified by flash column chromatography (petroleumether/EtOAc) to produce a colorless oil (4, 8.72 g, 87%).
84% With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0℃; for 4h; To a solution of <strong>[3929-47-3]3-(3,4-dimethoxyphenyl)propan-1-ol</strong> (3.6 g, 18.36 mmol) and CBr4 (6.09 g, 18.36 mmol) in DCM (20 mL) was added PPh3 (4.7 g, 18 mmol) and the reaction was stirred at 0 oC for 4 hrs. The reaction mixture was poured into H2O (100 mL) and extracted with DCM (50 mL x 3). The combined DCM layers were washed with brine (150 mL), dried over Na2SO4 and concentrated to dryness in vacuum. The residue was purified by silica gel column (PE/EA = 7/1) to give 4-(3-bromopropyl)-1,2-dimethoxybenzene (4 g, yield: 84%) as a colorless oil.
EXAMPLE 24A 1-Bromo-3-(3,4-dimethoxyphenyl)propane The title compound was prepared from <strong>[3929-47-3]3-(3,4-dimethoxyphenyl)-1-propanol</strong> as described in Journal of the American Chemical Society, 95, 8749 (1973), which is incorporated herein by reference, to provide the title compound. MS (DCI/NH3) m/e 276 (M+NH4)+.
With N-Bromosuccinimide; triphenylphosphine; In dichloromethane; at 20℃; for 16h;Ice-cooling; (18-2) Synthesis of 1-(3-bromopropyl)-3,4-dimethoxybenzene (compound 18-2) Compound 18-1 (2.00 g) was dissolved in methylene chloride (50 ml), triphenylphosphine (2.97 g) and N-bromosuccinimide (1.99 g) were added under ice-cooling, and the mixture was stirred under ice-cooling for 1 hr, and further at room temperature for 15 hr. The reaction mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. Diethyl ether (100 ml) was added, and the precipitated triphenylphosphine oxide was filtered off. The concentrate of the filtrate was purified by silica gel column chromatography (hexane:ethyl acetate=5:1 - 3:1) to give the object product (2.17 g) as a pale-brown oil. 1H-NMR(CDCl3) δ (ppm): 2.11-2.18(2H, m), 2.73(2H, t, J=7.3Hz), 3.40(2H, t, J=6.5Hz), 3.86(3H, s), 3.88(3H, s), 6.72-6.75(2H, m), 6.79-6.81(1H, m).

  • 2
  • [ 1634-04-4 ]
  • [ 3929-47-3 ]
  • [ 3945-85-5 ]
YieldReaction ConditionsOperation in experiment
With bromine; triphenylphosphine; In diethyl ether; cyclohexane; water; acetonitrile; A) 6.7 g of triphenylphosphine were dissolved in 200 ml of acetonitrile. After the solution had been cooled to 0 C., 1.3 ml of bromine were added dropwise. The cooling bath was then removed and a solution of 5 g of <strong>[3929-47-3]3-(3,4-dimethoxyphenyl)-1-propanol</strong> in 80 ml of acetonitrile was added dropwise. The reaction mixture was subsequently heated under reflux, using a water trap to remove 10 ml of distillate on several occasions over the course of 6 hours, replacing the amount removed with fresh acetonitrile. For working up, the solvent was evaporated off under reduced pressure, and the remaining residue was taken up in diethyl ether and filtered. The filtrate was concentrated under reduced pressure and purified by flash column chromatography using cyclohexane/methyl tert-butyl ether (7:2). 5.5 g of 3-(3,4-dimethoxyphenyl)-1-bromopropane were obtained as a colorless oil.
  • 3
  • [ 3929-47-3 ]
  • [ 3945-85-5 ]
  • 1-(3',4'-Dihydroxyphenyl)-4-(3'',4''-dimethoxyphenyl)-1-butene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With phosphorus tribromide; triphenylphosphine; EXAMPLE 21 Preparation of 1-(3,4-dihydroxyphenyl)-4-(3,4-dimethoxyphenyl)-1-butene In accordance with Examples 17-(1) and 17-(2), 1-(3,4-dihydroxyphenyl)-4-(3,4-dimethoxyphenyl)-1-butene was prepared. However, 3-(3,4-dimethoxyphenyl)propyl-1-triphenyl-phosphonium bromide synthesised from triphenylphosphine and 1-bromo-3-(3,4-dimethoxyphenyl)propane [this compound was synthesised from <strong>[3929-47-3]3-(3,4-dimethoxyphenyl)-1-propanol</strong> and phosphorus tribromide] was used as the Wittig reagent. IR: γmax 3340, 1605, 965 cm-1. NMR: δ(CDCl3), 2.0-2.5 (m, 2H), 2.60 (t, J=6 Hz, 2H), 3.9 (s, 6H), 5.55 (d, t, J=11, 7 Hz, 1H), 5.8 (s, 2H), 6.25 (d, J=11 Hz, 1H), 6.6-6.9 (m, 6H).
 

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