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Chemical Structure| 317318-96-0 Chemical Structure| 317318-96-0

Structure of 317318-96-0

Chemical Structure| 317318-96-0

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Product Details of [ 317318-96-0 ]

CAS No. :317318-96-0
Formula : C12H10F3NOS
M.W : 273.27
SMILES Code : OCC1=C(C)N=C(C2=CC=C(C(F)(F)F)C=C2)S1
MDL No. :MFCD03791170

Safety of [ 317318-96-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301-H318
Precautionary Statements:P280-P301+P310+P330-P305+P351+P338+P310
Class:6.1
UN#:2811
Packing Group:

Application In Synthesis of [ 317318-96-0 ]

* 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 [ 317318-96-0 ]

[ 317318-96-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 317318-96-0 ]
  • [ 439134-78-8 ]
YieldReaction ConditionsOperation in experiment
93% With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20℃; for 1h; [[4-METHYL-2- (4-TRIFLUOROMETHYL-PHENYL) THIAZOLE-5-YL]] methanol (15.0 g, 55.0 mmol) obtained from Example 2 was dissolved in anhydrous dichloromethane [(300] [MNo. ], and then triphenylphosphine (TPP, 5. 7 g, 60.0 mmol, 1.1 eq. ) and tetrabromomethane (20.0 [G,] 60.0 mmol, 1.1 eq. ) were added to the mixture [SEQUENCIALLY] at room temperature. After 1 hour, the solvent was evaporated from the reaction mixture under reduced pressure. Subsequently, the remained triphenylphosphine oxide was precipitated by a mixed solvent of hexane and ethyl acetate (v/v = [5/1),] followed by filtration and evaporation under reduced pressure to thereby yield [17. 2] g of the title compound (yield: 93percent). 'H-NMR (300 MHz, [CDC13)] : 8.00 (d, 2H, [J =] 8.1 Hz), 7.67 (d, 2H, [J =] 8.2 Hz), 4.72 (s, 2H), 2.47 (s, 3H). [13C-NMR] (78. [5] MHz, [CDC13)] : 165. 0, [153.] 8, [136. 9, 132. 4,] 129.7 (q), [127.] 0, 126.3 (m), 122.5, 23.8, 15.5.
93% With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20℃; for 1h;Product distribution / selectivity; [4-Methyl-2-(4-trifluoromethyl-phenyl)thiazole-5-yl]methanol (15.0 g, 55.0 mmol) obtained from Example 2 was dissolved in anhydrous dichloromethane (300 ml), and then triphenylphosphine (TPP, 15.7 g, 60.0 mmol, 1.1 eq.) and tetrabromomethane (20.0 g, 60.0 mmol, 1.1 eq.) were added to the mixture sequentially at room temperature. After stirring for 1 hour, the solvent was evaporated from the reaction mixture under reduced pressure. Subsequently, the remained triphenylphosphine oxide was precipitated by a mixed solvent of hexane and ethyl acetate (v/v = 5/1), followed by filtration and evaporation under reduced pressure to thereby yield 17.2 g of the title compound (yield: 93percent).1H-NMR (300 MHz, CDCl3): 8.00 (d, 2H, J = 8.1 Hz), 7.67 (d, 2H, J = 8.2 Hz), 4.72 (s, 2H), 2.47 (s, 3H).13C-NMR (75.5 MHz, CDCl3): 165.0, 153.8, 136.9, 132.4, 129.7 (q, J = 33 Hz), 127.0, 126.3 (q, J= 4 Hz), 122.5, 23.8, 15.5.
90.5% With N-Bromosuccinimide; triphenylphosphine; In dichloromethane; at 20℃; for 1h; [[4-METHYL-2-(4-TRIFLUOROMETHYL-PHENYL) THIAZOLE-5-YL] METHANOL (1 Q.] 0 [G,] [36.] 6 mmol) obtained from Example 2 was dissolved in anhydrous dichloromethane [300 ME,] and then triphenylphosphine (TPP, 10.6 g, [40. 3] mmol, [1.] [1] eq. ) and N- bromosuccinimide (7.17 g, 40.3 mmol, 1.1 eq. ) were added to the mixture at room temperature. After 1 hour, the solvent was evaporated from the reaction mixture under reduced pressure. Subsequently, the remained triphenylphosphine oxide was precipitated by a mixed solvent of hexane and ethyl acetate (v/v = [5/1),] followed by filtration and evaporation under reduced pressure to thereby yield [11. 1] g of the title compound (yield: 90.5percent).
90.5% With N-Bromosuccinimide; triphenylphosphine; In dichloromethane; at 20℃; for 1h;Product distribution / selectivity; Preparation of 5-bromomethyl-4-methyl-2-[(4-trifluoromethyl)phenyl]thiazole [Step C]: [4-methyl-2-(4-trifluoromethyl-phenyl)thiazole-5-yl]methanol (10.0 g, 36.6 mmol) obtained from Example 2 was dissolved in anhydrous dichloromethane 300 ml, and then triphenylphosphine (TPP, 10.6 g, 40.3 mmol, 1.1 eq.) and N- bromosuccinimide (7.17 g, 40.3 mmol, 1.1 eq.) were added to the mixture sequentially at room temperature. After stirring for 1 hour, the solvent was evaporated from the reaction mixture under reduced pressure. Subsequently, the remained triphenylphosphine oxide was precipitated by a mixed solvent of hexane and ethyl acetate (v/v = 5/1), followed by filtration and evaporation under reduced pressure to thereby yield 1 1.1 g of the title compound (yield: 90.5percent).
With N-Bromosuccinimide; triphenylphosphine; In tetrahydrofuran; at 10℃; for 0.75h; Example 4; Intermediate: 5-Bromomethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole; Cool (10°C) a solution of [4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]- methanol (Example 2, 753 mg, 3 mmol) in THF (12 mL) add triphenylphosphine (864 mg, 3.3 mmol) followed by freshly recrystallized N-bromosuccinimide (587 mg, 3.3 mmol). On complete addition, remove the cold bath and stir continuously for 45 min. Concentrate the resulting mixture under vacuum and purify the residue by flash chromatography (elute with 10percent ethyl acetate/ 10percent dichloromethane in heptane) to give the title compound as an orange solid (846 mg). MS (ESI) m/z 336,338 (M+H); Hl NMR (CDCl3) 8 2.48 (s, 3H), 4.72 (s, 2H), 7.69 (d, J = 8Hz, 2H), 8.01 (d, J = 8Hz, 2H).

 

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