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[ CAS No. 153171-22-3 ]

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Chemical Structure| 153171-22-3
Chemical Structure| 153171-22-3
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CAS No. :153171-22-3 MDL No. :MFCD04210206
Formula : C15H10BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :316.15 g/mol Pubchem ID :893620
Synonyms :

Safety of [ 153171-22-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 153171-22-3 ]

  • Upstream synthesis route of [ 153171-22-3 ]
  • Downstream synthetic route of [ 153171-22-3 ]

[ 153171-22-3 ] Synthesis Path-Upstream   1~8

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YieldReaction ConditionsOperation in experiment
100% at 100℃; for 6 h; (a) The reaction mixture of p-bromobenzyl bromide (corresponding to 50) (4.00g, 16.004mmol) and phthalimide potassium salt (3.26g, 17.61mmol) in DMF (10ml) was stirred for 6h at 100°C with a CaCl2 tube. After cooling, H2O (100ml) was added, and the resulting mixture was extracted with AcOEt (100ml×3). The combined organic layer was washed with H2O (100ml×1) and then brine (100ml×1), dried over Na2SO4 (anhyd), filtered, and concentrated under reduced pressure to afford 2-(4-bromobenzyl)isoindole-1,3-dione (5.28g, quant. y.) as a colorless solid. Colorless cotton-like crystal (n-hexane/AcOEt). Mp 126–129°C. 1H NMR (300MHz/CDCl3) δ 4.80 (2H, s, CH2), 7.32 (2H, d, J=7.8Hz, ArH), 7.44 (2H, d, J=8.1Hz, ArH), 7.71–7.73 (2H, m, ArH), 7.84–7.85 (2H, m, ArH).
Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 14, p. 3720 - 3731
[2] Chemistry - A European Journal, 2010, vol. 16, # 33, p. 10171 - 10177
[3] Journal of the Chemical Society, 1931, p. 1225,1232
[4] Tetrahedron, 1993, vol. 49, # 43, p. 9855 - 9866
[5] Patent: WO2015/103317, 2015, A1, . Location in patent: Page/Page column 271
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YieldReaction ConditionsOperation in experiment
53% With ammonium cerium (IV) nitrate In water; acetone at 20 - 25℃; for 0.666667 h; Inert atmosphere General procedure: A mixture of NHPI (266 mg, 1.63 mmol), arene 1aem (0.52e1.73 g, 3e10 mol per mole of NHPI), and acetone or CH2Cl2 (5 mL) (run 5) was purged with argon for 5 min. Then a solution of CAN (1.79 g, 3.26 mmol) in water (3 mL) was added with vigorous stirring for 10 min. The reaction mixturewas stirred at 20e25 C for 30 min. Thenwater (20 mL) was added to the reaction mixture, the mixture was extracted with CHCl3 (2 10 mL), and the combined organic extracts were successively washed with a saturated aqueous NaHCO3 solution (10 mL) and water (20 mL). The mixture was dried over MgSO4, and the solvent was removed using a water-jet vacuum pump. Products 2aem were isolated by column chromatography on SiO2 using CH2Cl2/EtOAc as the eluent with an increasing gradient of the latter from 0 to 20percent.4.6.8
N-(4-Bromobenzyl)phthalimide (2h)
88
White crystals; mp=133-136 °C (lit.
88
mp=143-145 °C); δH (300.13 MHz, CDCl3) 5.15 (s, 2H, CH2), 7.36-7.45 (m, 2H, ArH), 7.46-7.54 (m, 2H, ArH), 7.65-7.83 (m, 4H, ArH); δC (75.47 MHz, CDCl3) 79.1 (CH2), 123.6, 123.7, 128.9, 131.5, 131.8, 132.9, 134.6 (Ar), 163.5 (C=O).
Reference: [1] Tetrahedron, 2012, vol. 68, # 50, p. 10263 - 10271,9
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YieldReaction ConditionsOperation in experiment
95%
Stage #1: for 1 h; Milling
Stage #2: for 1 h; Milling
General procedure: A mixture of 50 mg of imide and the required amount of K2CO3 were placed in a 10 mL stainlesssteel grinding jar and milled for 1 hour at 30 Hz. Upon completion, the required amount of alkylhalide was added and milling was continued for 1 hour in the presence of 100 µL of dry DMF(LAG experiment, η = 2 µL mg-1). The obtained mixture was suspended in dichloromethane andwashed with water. The organic layers were collected and the solvent was evaporated. Where itwas necessary, the products were separated by using column chromatography
Reference: [1] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 1745 - 1752
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YieldReaction ConditionsOperation in experiment
85% With p-toluenesulfonic acid monohydrate; triethylamine In chloroform; toluene Example 1
Synthesis of Rhodamine-2-AM-DMAE-Bz STR6 4-Phthalimidomethyl bromobenzene
To a suspension of 10 g (44.94 mmol) of 4-bromobenzylamine hydrochloride in 200 ml of chloroform was added 12.5 ml (89.62 mmol) of triethylamine, followed by the addition of 8.99 g (60.67 mmol) of phthalic anhydride.
The mixture was stirred at room temperature for 10 minutes to give a homogeneous solution, which was then heated at 75° C. for three hours.
The reaction mixture was then evaporated to remove the chloroform and the residue was suspended in 400 ml of toluene followed by adding 700 mg of p-toluenesulfonic acid monohydrate.
The resulting mixture was briefly refluxed at 140° C., and additional 3 ml of triethylamine was added to form a homogeneous solution.
The solution was refluxed at 140° C. for 2 hours; and the water formed was collected through a Dean-Stark trap apparatus.
The solution was then cooled to room temperature, washed with 3percent sodium hydroxide (2*200 ml), water (1*200 ml), brine (1*200 ml), and dried over sodium sulfate.
Removal of the solvent under reduced pressure gave 12.07 g (85percent yield) of 4-phthalimidomethyl bromobenzene as a white solid. Rf: 0.6 (silica gel, ethyl acetate:hexane=1:2).
1 H NMR (CDCl3): δ ppm 4.79 (2H, s), 7.31, 7.44 (2H each, AA'BB'), 7.73, 7.84 (2H each, m).
Reference: [1] Patent: US6165800, 2000, A,
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Reference: [1] Angewandte Chemie - International Edition, 2007, vol. 46, # 43, p. 8266 - 8269
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Reference: [1] Organic Letters, 2018, vol. 20, # 18, p. 5610 - 5613
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Reference: [1] Patent: WO2006/81807, 2006, A2, . Location in patent: Page/Page column 16; 18; 23
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Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 14, p. 3720 - 3731
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