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Chemical Structure| 431-35-6 Chemical Structure| 431-35-6

Structure of 3-Bromo-1,1,1-trifluoroacetone
CAS No.: 431-35-6

Chemical Structure| 431-35-6

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Product Details of [ 431-35-6 ]

CAS No. :431-35-6
Formula : C3H2BrF3O
M.W : 190.95
SMILES Code : O=C(C(F)(F)F)CBr
MDL No. :MFCD00039237
InChI Key :ONZQYZKCUHFORE-UHFFFAOYSA-N
Pubchem ID :79008

Safety of [ 431-35-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H314
Precautionary Statements:P210-P280-P305+P351+P338-P310
Class:3(8)
UN#:2924
Packing Group:

Application In Synthesis of [ 431-35-6 ]

* 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.

  • Upstream synthesis route of [ 431-35-6 ]
  • Downstream synthetic route of [ 431-35-6 ]

[ 431-35-6 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 431-35-6 ]
  • [ 204319-69-7 ]
YieldReaction ConditionsOperation in experiment
58%
Stage #1: for 18 h; Heating / reflux
Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol; ethanol at 20℃; for 48 h;
A solution of3-brom-1, 1, 1-trifluoroacetone (3.2 ml, 30.2 mmol) and 2-amino-2- thioxoethyl pivalate (5.3 g, 30.2 mmol) in ethanol (15 ml) was stirred at reflux for 18 h. To the cooled solution were added methanol (10 ml) and DBU (4.6 ml, 30.2 mmol) and the solution was stirred at room temperature for 2 days. The reaction mixture was evaporated in vacuo, extracted with dichloromethane, washed with water, dried overNa2SO4, and evaporated in vacuo to give crude product as a black oil. This was purified by flash column chromatography on silica eluting with 30 percent ethyl acetate in hexane to give the title compound as an off-white solid (3.2 g, 58 percent).IH NMR (400 MHz, DMSO)8 8.42(1H, s), 6.30(1H, t, J5.8), 4.79 (2H, d, J5. 7).
58%
Stage #1: for 18 h; Heating / reflux
Stage #2: With methanol; 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol at 20℃; for 48 h;
A solution of 3-bromo- 1,1,1 -trifluoroacetone (3.2 ml, 30.2 mmol) and 2-(tert-butylcarbonyloxy) thioacetamide (5.3 g, 30.2 mmol) in ethanol (15 ml) was stirred at reflux for 18 h. To the cooled solution were added methanol (10 ml) and DBU (4.6 ml, 30.2 mmol) and the solution was stirred at room temperature for 2 days. The reaction mixture was evaporated in vacuo, extracted with dichloromethane, washed with water, dried over Na2SO4, and evaporated in vacuo to give crude product as a black oil. Purification by flash column chromatography, eluting with 30 percent ethyl acetate in hexane, gave the title compound as an off-white solid (3.2 g, 58 percent). 1H NMR (400 MHz, DMSO) δ 8.42 (1 H, s), 6.30 (1 H, t, J 5.8), 4.79 (2 H, d, J 5.7).
30%
Stage #1: at 60℃; for 24 h;
Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol at 20℃; for 48 h;
To the thioamide, 2-amino-2-thioxoethyl pivalate (3.0 g, 17.02 mmol) (Commercial source: Acros organics) in ethanol (10 ml), 3-bromo-l,l,l-trifluoropropan-2-one (3.23 g, 17.02 mmol) (Commercial source: Apollo scientific) was added and heated at 60°C for 24h. Then reaction mixture was cooled, DBU (2.59g, 17.02 mmol) was added and stirred at rt for 2d. Then volatiles were removed in vacuum, reaction mixture was partitioned between ethyl acetate and water. Organic layer was dried, evaporated and column purified to yield (4- (trifluoromethyl)thiazol-2-yl)methanol in 30percent yield.
References: [1] Patent: WO2005/49613, 2005, A1, . Location in patent: Page/Page column 52.
[2] Patent: WO2006/120481, 2006, A2, . Location in patent: Page/Page column 19.
[3] Patent: WO2012/54510, 2012, A1, . Location in patent: Page/Page column 90.
 

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