[ CAS No. 6942-39-8 ]

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Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 6942-39-8
Chemical Structure| 6942-39-8
Structure of 6942-39-8

Quality Control of [ 6942-39-8 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 6942-39-8 ]

SDS

Product Details of [ 6942-39-8 ]

CAS No. :6942-39-8MDL No. :MFCD00086167
Formula :C8H6BrFO2Boiling Point :247.5°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :233.03Pubchem ID :-
Synonyms :

Computed Properties of [ 6942-39-8 ]

TPSA : 26.3 H-Bond Acceptor Count : 3
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.13 Rotatable Bond Count : 2

Safety of [ 6942-39-8 ]

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 [ 6942-39-8 ]

  • Upstream synthesis route of [ 6942-39-8 ]
  • Downstream synthetic route of [ 6942-39-8 ]

[ 6942-39-8 ] Synthesis Path-Upstream   1~4

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YieldReaction ConditionsOperation in experiment
98% at 0℃; Methyl 2-bromo-5-fluorobenzoate (159-1). Trimethylsilyl diazomethane (338 ml, 676 mmol, 2.0 M in diethyl ether) was added dropwise to a stirred, 0°C solution of 2-bromo-5-fluorobenzoic acid (74 g, 338 mmol) in MeOH (676ml) until a yellow color persisted. Acetic acid was added dropwise until the yellow color dissipated. The solvent was removed in vacuo, and the resisdue was dissolved in CH2Cl2, then filtered through a plug of silica gel, eluting with CH2Cl2. The solvent was removed in vacuo to afford 77 g, 98 percent of 159-1 as a yellow oil.
98%
Stage #1: at 0℃;
Stage #2: With acetic acid In methanol; diethyl ether
Trimethylsilyl diazomethane (338 ml, 676 mmol, 2.0 M in diethyl ether) was added dropwise to a stirred, 0°C solution of 2-bromo-5-fluorobenzoic acid (74 g, 338 mmol) in MeOH (676ml) until a yellow color persisted. Acetic acid was added dropwise until the yellow color dissipated. The solvent was removed in vacuo, and the resisdue was dissolved in CH2Cl2, then filtered through a plug of silica gel, eluting with CH2Cl2. The solvent was removed in vacuo to afford 77 g, 98 percent of 2λ as a yellow oil.
Reference: [1] Patent: WO2008/51532, 2008, A1. Location in patent: Page/Page column 52-53
[2] Patent: WO2009/54925, 2009, A1. Location in patent: Page/Page column 20
  • 2
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YieldReaction ConditionsOperation in experiment
98% With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 23℃; for 48.00 h; Inert atmosphere DBU(1.7 equiv, 1.16 mL, 7.76 mmol) was added to a solution of 2-bromo-5-fluorobenzoic acid (1.0 equiv, 1.0 g, 4.57 mmol) and iodomethane (2.0 equiv, 0.57 mL, 9.14mmol) in CH3CN (11 mL) at 23 °C. After stirring for 48 h, thereaction was quenched with H2O (10 mL) and extracted with Et2O(2 x 10 mL). The combined organic extracts were washed with water (20 mL),brine (20 mL), dried over Na2SO4 and filtrated.Evaporation of the solvent under reduced pressure followed by flashchromatography (SiO2, 95/5 hexane/EtOAc) afforded the desired ester (1.0g, 98percent of yield) as a colorless oil. Rf = 0.50 (95/5 hexane/EtOAc); 1H NMR (400 MHz, CDCl3,25 °C): d 7.63 (dd, J= 8.8, 5.1 Hz, 1H), 7.53 (ddd, J =8.7, 3.1 Hz, 1H), 7.07 (ddd, J = 8.8, 7.6, 3.1 Hz, 1H), 3.94 (s, 3H)ppm.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 20, p. 4393 - 4398
[2] Patent: WO2010/135560, 2010, A1. Location in patent: Page/Page column 135-136
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YieldReaction ConditionsOperation in experiment
97% for 24.00 h; Preparation 6; test-butyl [2- (aminomethyl)-4-fluorobenzyl] carbamate; (a) Methyl 2-bromo-5-fluorobenzoate; To a solution of 2-bromo-5-fluorobenzoic acid (3.0 g, 13.7 mmol) in methanol (4 mL) was added HCl-saturated methanol (70 mL). The reaction mixture was stirred for 24 hours and then concentrated. The excess of HC1 was removed by co-evaporation from methanol to give the sub-title compound (97percent), which was used in the next step without further purification. 1H NMR (500 MHz, CDC13) 6 3.96 (s, 3H), 7.09 (dt, 1H), 7.55 (dd, 1H), 7.65 (dd, 1H)
84.7% for 4.00 h; Reflux General procedure: To a solution of 2-bromo-4-fluorobenzoic acid (2.17 g, 10.00 mmol) in methanol (10 mL) was added sulfuric acid (1.63 mL, 30 mmol) , the reaction mixture was refluxed for 4 h.The solvent was removed in vacuo.The mixture was diluted with diethyl ether, and washed water (50 mL * 3) and brine (50 mL * 3), dried over MgSO4. The solvent was removed under reduced pressure.The residue was purified by flash column chromatography with petroleum ether-ethyl acetate (80/1) as eluant to afford colorless liquid. Yield: 88.3percent.This compound was prepared according to the general procedure reported by Baker.13 The spectral data were consistent with that reported in the literature.
50 g for 8.00 h; Reflux; Inert atmosphere In the nitrogen atmosphere,2-bromo-5-fluorobenzoic acid (50.0 g) was added,Sulfuric acid (7 ml) and methanol (500 ml) was stirred at reflux temperature for 8 hours.After the reaction solution was cooled to room temperature,The methanol was distilled off under reduced pressure,And then an aqueous solution of ethyl acetate and sodium hydrogencarbonate was added thereto to carry out liquid separation.The solvent of the organic layer was evaporated under reduced pressure to give methyl 2-bromo-5-fluorobenzoate (50.0 g).
2.7 g at 0 - 68℃; for 18.00 h; Step 1. methyl 2-bromo-5-fluorobenzoate (0904) (0905) To a solution of 2-bromo-5-fluorobenzoic acid (4.00 g, 18.26 mmol) in MeOH (120 mL, anhydrous) was added SOCl2 (3.26 g, 27.40 mmol) dropwise at 0 °C and the mixture was heated at 68 °C for 18 h. TLC (petroleum ether: EtOAc = 5:1) confirmed the desired product. The mixture was concentrated and the residue was mixed with EtOAc (200 mL), washed by NaHCO3 (150 mL), brine (150 mL), dried over anhydrous Na2SO4, filtered and concentrated to give methyl 2-bromo-5-fluorobenzoate as a colorless oil. Yield: 2.7 g LCMS method C: Rt = 0.77 min.

Reference: [1] Journal of Organic Chemistry, 2005, vol. 70, # 11, p. 4354 - 4359
[2] Patent: WO2005/75424, 2005, A1. Location in patent: Page/Page column 114
[3] Journal of Labelled Compounds and Radiopharmaceuticals, 2007, vol. 50, # 4, p. 245 - 250
[4] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 24, p. 7101 - 7111
[5] Journal of the American Chemical Society, 2010, vol. 132, # 41, p. 14412 - 14414
[6] Patent: US2009/215728, 2009, A1. Location in patent: Page/Page column 52
[7] Patent: US2011/160212, 2011, A1. Location in patent: Page/Page column 19
[8] Patent: TWI574948, 2017, B. Location in patent: Page/Page column 118
[9] Patent: WO2017/214367, 2017, A1. Location in patent: Page/Page column 187
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Reference: [1] Patent: US2004/220273, 2004, A1. Location in patent: Page 16
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