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Chemical Structure| 1221171-97-6 Chemical Structure| 1221171-97-6

Structure of 1221171-97-6

Chemical Structure| 1221171-97-6

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Product Details of [ 1221171-97-6 ]

CAS No. :1221171-97-6
Formula : C7H3ClF3NO3
M.W : 241.55
SMILES Code : O=C(C1=CC(Cl)=NC(OC(F)(F)F)=C1)O
MDL No. :MFCD22571780

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Application In Synthesis of [ 1221171-97-6 ]

* 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 [ 1221171-97-6 ]

[ 1221171-97-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 124-38-9 ]
  • [ 1221171-96-5 ]
  • [ 1221171-97-6 ]
YieldReaction ConditionsOperation in experiment
71% 2-Chloro-6-trifluoromethoxy isonicotinic acid (43); At 0 0C, butyllithium (1.56 M in hexane, 4.0 mL, 6.2 mmol, 0.67 eq) was added dropwise to a solution of butylmagnesium chloride (2M in THF, 1.5 mL, 3.0 mmol, 0.33 eq) in THF (8 mL), followed after 10 min by a solution of 2-chloro-4-iodo-6- trifluoro?iepsilonthoxypyridinepsilon (42, 3.0 g, 9.3 mmol, 1 eq) in THF (5 mL). After 10 min the reaction mixture was poured onto an excess of freshly crushed dry ice before being treated with an aqueous solution of sodium hydroxide (5%, 15 mL). The resulting aqueous layer was collected, washed with diethylether (10 mL) and acidified to pH 4 by dropwise addition of hydrochloric acid (6 N, 5 mL). After extraction with ethyl acetate (3 x 10 mL), the combined organic layers were dried over sodium sulfate before being evaporated to afford pure 2-chloro-6-trifluoromethoxy isonicotinic acid (43, 1.6 g, 6.6 mmol, 71%) as a white powder; m.p. 65-68 0C.1H NMR (CDCl3, 300 MHz): delta = 10.12 (br s, 1 H), 7.88 (d, J = 0.9 Hz, 1 H), 7.56 (d, J = 0.9 Hz, 1 H). - 19F NMR (CDCl3, 282 MHz): delta = -57.3 - 13C NMR (CDCl3, 75 MHz): delta = 167.6, 156.3, 150.4, 143.0, 122.5, 120.2 (q, J = 260 Hz), 113.5. - C7H3ClF3NO3 (241): calcd. (%) C 34.81, H 1.25, N 5.80; found C 34.64, H 1.55, N 5.76.
  • 2
  • [ 1221171-97-6 ]
  • [ 1221171-98-7 ]
YieldReaction ConditionsOperation in experiment
81% With ammonium formate;palladium 10% on activated carbon; In methanol; at 55.0℃; for 16.0h; 2-Trifluoromethoxy isonicotinic acid (44); At 25 0C, palladium (10% on charcoal, 330 mg) was added with stirring to a solution of 2-chloro-6-trifluoromethoxy isonicotinic acid (43, 1.1 g, 4.55 mmol) and ammonium formate (574 mg, 9.1 mmol, 2 eq) in methanol (8 mL). The reaction mixture was stirred for 16 h at 55 0C before being filtrated under suction and the filtrate evaporated. The residue was partitioned between ethyl acetate (2x 15 mL) and 2.0 M hydrochloric acid(20 mL). The combined organic layers were dried over sodium sulfate before being evaporated to afford pure 2-trifluoromethoxy isonicotinic acid (44, 760 mg, 3.7 mmol,81%) as a white powder; m.p. 149-152 0C.1H NMR (CD3OD, 300 MHz): delta = 8.39 (d, J = 5.1 Hz, 1 H), 7.77 (dd, J= 5.1, 1.0 Hz, 1H), 7.51 (d, J= 1.0 Hz, 1 H). - 19F NMR ((CD3)2CO, 282 MHz): delta = -57.6 - 13C NMR(CD3OD, 75 MHz): delta = 164.9, 157.2, 148.4, 143.3, 121.8, 120.3 (q, J= 260 Hz), 112.5. - C7H4F3NO3 (207): calcd. (%) C 40.59, H 1.95, N 6.76; found C 40.28, H 2.21, N 6.67.
 

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