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[ CAS No. 337536-15-9 ]

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2D
Chemical Structure| 337536-15-9
Chemical Structure| 337536-15-9
Structure of 337536-15-9 *Storage: {[proInfo.prStorage]}

Quality Control of [ 337536-15-9 ]

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Related Doc. of [ 337536-15-9 ]

SDS

Product Details of [ 337536-15-9 ]

CAS No. :337536-15-9MDL No. :MFCD09701286
Formula :C8H6BrNOBoiling Point :449°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :212.04Pubchem ID :21907509
Synonyms :

Computed Properties of [ 337536-15-9 ]

TPSA : 29.1 H-Bond Acceptor Count : 1
XLogP3 : 1.5 H-Bond Donor Count : 1
SP3 : 0.13 Rotatable Bond Count : 0

Safety of [ 337536-15-9 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P280-P305 P351 P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 337536-15-9 ]

  • Upstream synthesis route of [ 337536-15-9 ]
  • Downstream synthetic route of [ 337536-15-9 ]

[ 337536-15-9 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 337536-14-8 ]
  • [ 337536-15-9 ]
YieldReaction ConditionsOperation in experiment
99% With ammonia In tetrahydrofuran; methanol at 0 - 20℃; for 7.50 h; 3-bromo-2-methylbenzoic acid (6.13 g, 28.5 mmol) was suspended in MeOH (52 ml) and concentrated H2SO4 (10.0 ml) was added via syringe over 4 minutes at room temperature. The reaction was heated to 90 C, stirred for 4 hours, cooled in an ice water bath, and then quenched with saturated NaHCO3 (250 ml). The reaction was extracted with EtOAc (3 x 50 ml), and the organic layers were combined, dried over MgSO4, filtered, and concentrated to give methyl 3-bromo-2-methylbenzoate (6.43 g, 98percent).Methyl 3-bromo-2-methylbenzoate (7.45 g, 32.5 mmol) was dissolved in CCl4 (94 ml) and N- bromosuccinimide (6.67 g, 37.5 mmol) and benzoyl peroxide (0.38 g, 1.6 mmol) were added. The reaction was heated to 75 C - 85 C, stirred for 3 hours and 45 minutes, cooled to room temperature, and filtered. The filtrate was concentrated and purified on SiO2 (Biotage instrument; 0percent -> 20percent EtOAc / hexanes) to give methyl 3-bromo-2-(bromomethyl)benzoate (10.07 g, 100percent).Methyl 3-bromo-2-(bromomethyl)benzoate (10.30 g, 33.44 mmol) was dissolved in THF (93 ml) and cooled in an ice water bath. Then, ΝH3 (60 ml, ~ 7N in MeOH) was added via syringe over 4.5 minutes. The reaction was warmed to room temperature, stirred for 7.5 hours, and then diluted with water. The aqueous phase was extracted repeatedly with CH2Cl2 and EtOAc. The organic extracts were combined, dried over sodium sulfate, filtered, and concentrated to give title compound (6.99 g, EPO 99percent) as a white powder. MS (ESI pos. ion) m/z: 212.0 (M+H). Calc'd Exact Mass for C8H6BrNO: 211.
91% With ammonia In tetrahydrofuran; water at 20℃; Step 3:
4-bromoisoindolin-1-one
To a solution of methyl 3-bromo-2-(bromomethyl)benzoate (27 mmol) in THF (100 mmol) was added ammonium hydroxide (9 mL) dropwise at rt.
The reaction mixture was allowed to stir overnight and then diluted with 30 mL of water.
The solution was extracted with DCM, dried over Na2SO4, filtered and concentrated to give 4-bromoisoindolin-1-one (5.20 g, 91percent).
80% With ammonia In tetrahydrofuran; water at 20℃; for 18.00 h; To a solution of the 3-bromo-2-bromomethyl-benzoic acid methyl ester (2.74 g, 8.88 [MMOL)] in tetrahydrofuran (70 [ML)] at [0°C] was added 30 percent aq. ammonia (10 ml) and the mixture stirred at room temperature under nitrogen for 18 hours. The solvent was removed by evaporation under reduced pressure. The white residue was partitioned between ethyl acetate (50 mi) and 2M citric acid (50 [ML).] The ethyl acetate was dried magnesium sulfate, filtered and solvent removed by evaporation under reduced pressure. The orange oil was dissolved in minimum [DICHLOROMETHANE] and purified by flash chromatography on silica gel eluting with a solvent gradient of [DICHOROMETHANE/METHANOL] (9: 1) to give the title compound (1.5 g, 80 percent) as a white solid. [1H-NMR] (400 MHz, DMSO): [A] = 4.29 (s, 2H), 7.44 (t, [1H),] 7.69 (d, [1H),] 7.80 (d, [1H),] 8.68 (brs, 1 H). LRMS (Electrospray) : m/z [M+ 2H] [+] 214. Microanalysis : Found: C, 45.20 ; H, 2.90 ; N, 6.67. C8H6NOBr requires C, 45.31 ; H, 2.85 ; N, 6.60percent.
4.14 g With ammonium hydroxide In tetrahydrofuran at 20℃; Inert atmosphere Step 3: Preparation of 4-bromoisoindolin-1-one (4) To a solution of methyl 3-bromo-2-(bromomethyl)benzoate 3 (8.3 g, 26.9 mmol) in THF (100 mL) was added concentrated NH4OH (9 mL) dropwise. After stirring them at room temperature overnight, the mixture was concentrated in vacuo to give the residue, which was then washed with water and MTBE, and dried to give the title product 4 (4.14 g). 1H NMR (400 Hz, CDCl3) δ 7.85-7.83 (d, J=7.5 Hz, 1H), 7.72-7.70 (d, J=7.9 Hz, 1H), 7.42-7.38 (t, J=7.7 Hz, 1H), 6.81 (s, 1H), 4.39 (s, 2H).

Reference: [1] Patent: WO2007/5668, 2007, A2. Location in patent: Page/Page column 36-37
[2] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 6, p. 3091 - 3107
[3] Patent: US2008/171754, 2008, A1. Location in patent: Page/Page column 104
[4] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 17, p. 4505 - 4509
[5] Patent: WO2004/14357, 2004, A2. Location in patent: Page/Page column 39-40
[6] Patent: US6518257, 2003, B1
[7] Patent: US2005/26976, 2005, A1. Location in patent: Page/Page column 11
[8] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 11, p. 3036 - 3040
[9] Patent: US2016/311772, 2016, A1. Location in patent: Paragraph 0637; 0642; 0643
[10] Patent: WO2004/108672, 2004, A1. Location in patent: Page 22; 23
  • 2
  • [ 1291713-01-3 ]
  • [ 1972-28-7 ]
  • [ 337536-15-9 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 21, p. 3707 - 3712
  • 3
  • [ 99548-54-6 ]
  • [ 337536-15-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 17, p. 4505 - 4509
[2] Patent: US2016/311772, 2016, A1
[3] Patent: WO2004/108672, 2004, A1
  • 4
  • [ 76006-33-2 ]
  • [ 337536-15-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 17, p. 4505 - 4509
[2] Patent: US2016/311772, 2016, A1
[3] Patent: WO2004/108672, 2004, A1
  • 5
  • [ 21900-48-1 ]
  • [ 337536-15-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 17, p. 4505 - 4509
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