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[ CAS No. 164365-88-2 ]

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Chemical Structure| 164365-88-2
Chemical Structure| 164365-88-2
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Product Details of [ 164365-88-2 ]

CAS No. :164365-88-2 MDL No. :MFCD06201020
Formula : C9H18BrNO2 Boiling Point : 308.8°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :252.15 g/mol Pubchem ID :10868765
Synonyms :

Safety of [ 164365-88-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 164365-88-2 ]

  • Upstream synthesis route of [ 164365-88-2 ]
  • Downstream synthetic route of [ 164365-88-2 ]

[ 164365-88-2 ] Synthesis Path-Upstream   1~10

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Reference: [1] Synthetic Communications, 1999, vol. 29, # 15, p. 2685 - 2693
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  • [ 75178-87-9 ]
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YieldReaction ConditionsOperation in experiment
100% With carbon tetrabromide; triphenylphosphine In tetrahydrofuran for 3 h; Inert atmosphere tert-Butyl (4-hydroxybutyl)carbamate (1.06 g, 5.788 mmol) was dissolved in dry THF (54 ml) followed by addition of Ph3P (2.86 g, 10.92 mmol, 1.9 eq.). Then CBr4 (3.62 g, 10.92 mmol, 1.9 eq.) was slowly added to the mixture. After 3 h the solution was filtered through a celite pad to eliminate the by-products and washed with Et2O. The solvents were removed under high vacuum. The crude product was purified by flash chromatography on silica gel (hexane/EtOAc, 3:1) to give 9 as a white solid at 5°C (1.73 g, quantitative yield)
98% With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 4 h; To a solution of tert-butyl (4-hydroxybutyl)carbamate (5a) (1.0 g, 5.3 mmol) and PPh3 (2.09 g, 8 mmol) in 20 mL of THF, a solution of CBr4 (2.7 g, 8 mmol) in 10 mL of THF was added dropwise, under stirring, at 0 °C. The mixture was allowed to warm to room temperature and stirred for 4 h. The solvent was evaporated in vacuo, then the residue was purified by silica gel flash chromatography, eluting with hexanes, then hexanes/ethyl acetate, from 95/5 to 8/2, affording 1.31 g (5.2 mmol, 98percent yield) of pure, target product, as a colorless oil.‘H NMR (400 MHz, CDC13): = 4.54 (bs, 1 H); 3.44 (t, 2 H); 3.17-3.14 (m, 2 H); 1.92-1.87 (m, 2 H); 1.69-1.63 (m, 2 H); 1.46 (s, 9 H).
78% With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 20 h; Inert atmosphere A solution of compound 07-4-1 (11.0 g, 58.1 mmol, 1.0 eq) in DCM (200 mL) were added CBr4 (39.5 g, 119.1 mmol, 2.05 eq) and PPh3 (32.9 g, 125.6 mmol, 2.16 eq) at 20°C, and the resulting mixture was stirred at 20°C for 20 h, diluted with water (100 mL) and extracted with DCM (100 mL*3) ,and the mixture was filtered and concentrated under reduced pressure to give a residue which was purified by column chromatography (SiO2) to give compound 07-4-2 (12.0 g, 45.2 mmol, 78percent yield).1H NMR (CDCl3, 400 MHz): δ 3.41 (t, J=6.62 Hz, 2 H), 3.14 (d, J=6.17 Hz, 2 H), 1.83 - 1.94 (m, 2 H), 1.62 (quin, J=7.28 Hz, 2 H), 1.36 - 1.49 (m, 9 H).
63.3% With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃; for 18 h; To an ice-cold solution of tert-butyl 4-hydroxybutylcarbamate (5 g, 26.41 mmol) in dichloromethane (200 mL) was added triphenylphosphine (10.38 g, 39.61 mmol) followed by carbon tetrabromide (13.15 g, 39.61 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 18 h. The solvent was removed under reduced pressure and the residue was purified by column chromatography (60-120 mesh silica gel) using 10percent ethyl acetate in pet-ether to give tert-butyl 4-bromobutylcarbamate(4.2 g, 63.3 percent) as a light green liquid. XH NMR (400 MHz, CDC13) δ ppm 4.53 (1H, s), 3.45-3.41 (2H, m), 3.18-3.13 (2H, m), 1.93-1.83 (2H, m), 1.68-1.61 (2H, m), 1.47 (9H, s).

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 1151 - 1155
[2] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 11, p. 1156 - 1161
[3] Patent: WO2017/53360, 2017, A1, . Location in patent: Paragraph 0154
[4] Patent: WO2017/96045, 2017, A1, . Location in patent: Paragraph 00884
[5] Patent: WO2012/9309, 2012, A1, . Location in patent: Page/Page column 58
[6] Journal of the Chemical Society - Series Chemical Communications, 1995, # 10, p. 1015 - 1016
[7] Journal of the Chemical Society, Perkin Transactions 2, 2002, # 5, p. 923 - 927
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YieldReaction ConditionsOperation in experiment
70% With triphenylphosphine In dichloromethane 7b)
tert-Butyl 4-bromobutylcarbamate
Carbon tetrabromide (5 g) was added at once to a solution of tert-butyl 4-hydroxybutylcarbamate (1.89 g) obtained in Example 7a) and triphenylphosphine (3.15 g) in methylene chloride (20 ml), and the mixture was further stirred at room temperature for 2 minutes.
The reaction mixture was washed by addition of saturated sodium bicarbonate water, followed by further washing with saturated brine.
The extract was concentrated, and the residue was purified by silica gel column to obtain the title compound as colorless oil (1.76 g, 70percent).
NMR (CDCl3) δ: 1.46 (9H, s), 1.50-2.00 (4H, m), 3.08-3.12 (2H, m), 3.43 (2H, t, J=6.6).
Reference: [1] Patent: US2003/187023, 2003, A1,
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YieldReaction ConditionsOperation in experiment
5.387 g With dmap; di-<i>tert</i>-butyl dicarbonate; triethylamine In dichloromethane at 20℃; for 1.5 h; The 5 g 4 - the bromine is positive butane -1 - ammonia hydrobromide with 4.686 g (1.5 eq) carbonic acid di-tert-butyl dicarbonate dissolved in two in the methylene chloride solution, stirring and dissolving, slowly dropping containing 193 mg (0.1 eq) 4 - dimethylamino pyridine and 8.688 g (4 eq) methylene dichloride solution of triethylamine, the reaction at room temperature for 1.5 h. Finally in the separatory funnel for respectively 0.5 N hydrochloric acid aqueous solution and saturated salt water washing the reaction solution, after drying by anhydrous sodium sulfate, filtered, reduced pressure distillation to remove the organic solvent, to obtain 5.387 g intermediate II.
Reference: [1] Patent: CN108530391, 2018, A, . Location in patent: Paragraph 0038-0040
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  • [ 4509-90-4 ]
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Reference: [1] Organic Preparations and Procedures International, 2004, vol. 36, # 2, p. 141 - 149
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Reference: [1] Synthetic Communications, 1999, vol. 29, # 15, p. 2685 - 2693
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Reference: [1] Inorganic Chemistry, 2011, vol. 50, # 14, p. 6472 - 6481
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  • [ 24424-99-5 ]
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 2, 2002, # 5, p. 923 - 927
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 1151 - 1155
[3] Patent: WO2017/96045, 2017, A1,
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Reference: [1] Synthetic Communications, 1999, vol. 29, # 15, p. 2685 - 2693
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 2, 2002, # 5, p. 923 - 927
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