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[ CAS No. 877151-07-0 ]

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2D
Chemical Structure| 877151-07-0
Chemical Structure| 877151-07-0
Structure of 877151-07-0 *Storage: {[proInfo.prStorage]}

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Product Details of [ 877151-07-0 ]

CAS No. :877151-07-0MDL No. :MFCD28662779
Formula : C9H8FIO2 Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :294.06Pubchem ID :-
Synonyms :

Computed Properties of [ 877151-07-0 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 877151-07-0 ]

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Application In Synthesis of [ 877151-07-0 ]

  • Downstream synthetic route of [ 877151-07-0 ]

[ 877151-07-0 ] Synthesis Path-Downstream   1~8

  • 2
  • [ 321-21-1 ]
  • [ 74-88-4 ]
  • [ 877151-07-0 ]
YieldReaction ConditionsOperation in experiment
63% Example 3; Step l+ eMethyl 4-fluoro-2-iodo-6-methylbenzoate4-Fluoro-2-methylbenzoic acid (5.0 gr, 32.4 mmol), palladium(ll) acetate (0.364 g, 1.62 mmol), iodobenzene diacetate (12.54 g, 38.92 mmol) and elemental iodine (9.88 g, 38.92 mmol) were dissolved in N, N- dimethylformamide (130 mL) and stirred at 1000C overnight. The reaction mixture was cooled to room temperature, diluted with methyl-ferf-butylether and aqueous hydrochloric acid and washed with 10% sodium metabisolfite aqueous solution. Organic phase was treated with 2N aqueoussodium hydroxide. The resulting aqueous phase was treated with aqueous hydrochloric acid up to acidic pH and extracted with methyl-ferf-butylether. The organic phase was washed with brine, dried over sodium sulfate and concentrated. So obtained iodinated benzoic acid (6.9 g, 24.6 mmol) was dissolved in N,N-dimethylformamide (50 mL) and metyliodide (3 mL, 49.2 mmol) and potassium carbonate (5 g, 36.9 mmol) were added. The reaction mixture was stirred overnight at room temperature, diluted with methyl-ferf-butylether and washed with water, 1M sodium hydroxide, water and brine. Solvent was removed under reduced pressure and the crude was purified by flash chromatography (n-hexane/diethyl ether 100:2) to give title compound (5.9 g, 63% yield). 1H NMR (400 MHz, DMSOd6) delta ppm 2.27 (s, 3 H) 3.86 (s, 3 H) 7.21 - 7.27 (m, 1 H) 7.63 (m, J=8.18, 2.44, 0.40,0.40, 0.40 Hz, 1 H).
  • 3
  • [ 1048025-60-0 ]
  • [ 80-48-8 ]
  • [ 877151-07-0 ]
YieldReaction ConditionsOperation in experiment
81% To a solution of 4-fluoro-2-iodo-6-methyl-benzoic acid (VII) (30.05 g, 0.109 mol) in N,N-dimethylformamide (300 mL) was added anhydrous potassium carbonate (22.0 g, 0.16 mol) under efficient magnetic stirring. After 15 mm methyl p-toluensulfonate (30.7 g, 0.16 mol) was added. The brown suspension was stirred at room temperature for 2 h.Potassium acetate (12.4 g, 0.13 mol) was then added to destroy the unreacted methyl p-toluensulfonate and the mixture was stirred overnight. The thick reaction mixture was diluted with methyl-tert-butylether (100 mL) and washed with water (600 mL); the aqueous layer was separated and extracted twice with methyl-tert-butylether (70 mL x 2). The combined organic extracts were washed with brine (50 mL), dried over Na2SO4 and concentrated under reduced pressure to a solid residue. This material was purified by chromatography (eluant n-hexane/ethyl acetate 9:1),affording 26.2 g (81%) of product as colorless oil.1H NMR (400.5 MHz, DMSO-d6) ppm 2.27 (s, 3 H), 3.86 (s, 3 H), 7.25 (dd, JHF 9.6, JHH 2.4 Hz, 1 H), 7.63 (dd,JHF = 8.2, JHH = 2.4 Hz, 1 H).
  • 4
  • [ 877151-07-0 ]
  • [ 1606995-44-1 ]
  • 5
  • [ 877151-07-0 ]
  • [ 1606995-45-2 ]
  • 6
  • [ 877151-07-0 ]
  • [ 1606995-46-3 ]
  • 7
  • [ 877151-07-0 ]
  • [ 1606995-47-4 ]
  • 8
  • [ 877151-07-0 ]
  • copper(l) cyanide [ No CAS ]
  • [ 877151-43-4 ]
YieldReaction ConditionsOperation in experiment
70% In N,N-dimethyl-formamide; at 110℃; for 5h; A solution of <strong>[877151-07-0]4-fluoro-2-iodo-6-methyl-benzoic acid methyl ester</strong> (VI) (26.02 g, 88.48 mmol) in 260 mL of N,Ndimethylformamide was treated with copper(I) cyanide (12.18 g; 0.136 mol) and stirred at 11000 for 5 h. The darkcolored mixture was allowed to cool to about 60C, treated with 105 g of Celite 560 coarse (Fluka) under efficient stirring and diluted with ethyl acetate (250 mL). After cooling to room temperature, the mixture was slowly poured in 0.25N aqueous sodium hydroxide (500 mL) and then filtered. The reaction flask and the panel were washed with ethyl acetate (100 mL). The aqueous layer was separated and extracted twice with ethyl acetate (250 mL + 100 mL). The combined organic extracts were washed with brine (200 mL), dried over Na2SO4 and concentrated underreduced pressure to give 22.00 g of raw product as yellow solid. This material was crystallized from n-hexane (40 mL): after cooling to room temperature the solid was collected by filtration and the mother liquors were concentrated under reduced pressure. The solid residue so obtained was crystallized from n-hexane (20 mL) yielding, after filtration of the solids, a second crop of product. The combined crops (14.15 g) were finally purified by chromatography eluting in gradient from n-hexane / methyl-tert-butylether 9:1 to n -hexane / ethyl acetate 9:1. Afterevaporation of the fractions 12.0 g (70%) of 2-cyano-4-fluoro-6-methyl-benzoic acid methyl ester (V) were obtained.1H NMR (400.5 MHz, DMSO-d6) ppm 2.42 (s, 3H), 3.93 (s, 3H), 7.65 (dd, JHF 9.6, JHH 2.6 Hz, 1H), 7.85 (dd, JHF8.3, 2.6 Hz, 1H).
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