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Chemical Structure| 83189-97-3 Chemical Structure| 83189-97-3

Structure of 83189-97-3

Chemical Structure| 83189-97-3

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Product Details of [ 83189-97-3 ]

CAS No. :83189-97-3
Formula : C7H4BrF2NO3
M.W : 268.01
SMILES Code : O=[N+](C1=CC=C(OC(F)F)C(Br)=C1)[O-]
MDL No. :MFCD18390952
InChI Key :PIKNQJGOLAQCBJ-UHFFFAOYSA-N
Pubchem ID :13314704

Safety of [ 83189-97-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 83189-97-3 ]

* 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 [ 83189-97-3 ]

[ 83189-97-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 5847-59-6 ]
  • 3-bromo-4-difluoromethoxyaniline [ No CAS ]
  • [ 83189-97-3 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In 1,4-dioxane; water; EXAMPLE 1 Production of 3-bromo-4-difluoromethoxyaniline: <strong>[5847-59-6]2-Bromo-4-nitrophenol</strong> (10.9 g) was dissolved in dioxane (60 ml), a solution of sodium hydroxide (18.4 g) in water (50 ml) was added thereto, and the resulting mixture was heated up to 60 C. while stirring vigorously. Chlorodifluoromethane gas was introduced therein, whereby the generation of heat was initiated. The reaction was continued for about 40 minutes. The reaction mixture was cooled to room temperature, poured onto ice-water and extracted with ether. The extract was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 3-bromo-4-difluoromethoxynitrobenzene (8.7 g) as a pale yellow oil. nD20.5 1.5500. NMR deltaCDCl 3 (ppm): 6.68 (1H, t, J=72 Hz), 7.33 (1H, d, J=9 Hz), 8.21 (1H, d.d., J=9 Hz, 3 Hz), 8.45 (1H, d, J=3 Hz).
  • 2
  • [ 5847-59-6 ]
  • [ 653-13-4 ]
  • [ 83189-97-3 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 7; 2-Difluoromethoxy-N-(3-piperazin-1-yl-4-difluoromethoxy-phenyl)-benzenesulfonamide TrifluoroacetateThe compound was prepared starting from commercially available <strong>[5847-59-6]2-bromo-4-nitrophenol</strong>, which was reacted with 2-chloro-2,2-difluoroacetophenone (J. Hu et al., J. Org. Chem., 2006, 71, 9845) to yield 2-bromo-1-difluoromethoxy-4-nitro-benzene. Subsequent Buchwald-Hartwig coupling of 2-bromo-1-difluoromethoxy-4-nitro-benzene with tert.butyloxycarbonyl-piperazine by analogy to preparation example 3.1, reduction of the nitro group to the corresponding aniline by analogy to preparation example 3.2, subsequent coupling with commercially available 2-difluoromethoxybenzene-sulfonylchloride by analogy to preparation example 1.4, and final deprotection under acidic conditions by analogy to example 1 yielded the title compound.ESI-MS:450.1 [M+H]+ 1H-NMR (DMSO-d6, 400 Hz): delta [ppm] 10.4 (s, 1H), 8.7 (s, broad, 2H), 7.9 (d, 1H), 7.7 (t, 1H), 7.4 (m, 2H), 7.3 (t, 1H), 7.0 (t, 1H), 7.0 (d, 1H), 6.8 (s, 1H), 6.75 (d, 1H), 3.2 (broad, 4H), 3.0 (broad, 4H).
 

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