[ CAS No. 79538-03-7 ] 2,3,5,6-Tetrafluoro-4-methylbenzyl Alcohol

Cat. No.: A222015

2D 3D

Structure of 79538-03-7 * Storage: Sealed in dry,Room Temperature

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Quality Control of [ 79538-03-7 ]

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Specification

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Product Details of [ 79538-03-7 ]

CAS No. :	79538-03-7	MDL No. :	MFCD03093260
Formula :	C₈H₆F₄O	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	PJCSTULKVNHEGW-UHFFFAOYSA-N
M.W :	194.13	Pubchem ID :	2734209
Synonyms :

Safety of [ 79538-03-7 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 79538-03-7 ]

* 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 [ 79538-03-7 ]

[ 79538-03-7 ] Synthesis Path-Downstream 1~24

1
[ 79538-03-7 ]
[ 4489-14-9 ]
[ 223419-26-9 ]

Reference： [1]Bioscience, Biotechnology and Biochemistry,2004,vol. 68,p. 170 - 174

2
(Z)-(1R)-trans-2,2-dimethyl-3-(1-propenyl)cyclopropanecarboxylic acid [ No CAS ]
[ 79538-03-7 ]
(2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R,3R)-2,2-dimethyl-3-((1Z)-1-propenyl)cyclopropanecarboxylate [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2007,vol. 128,p. 1174 - 1181

3
[ 79538-03-7 ]
[ 240494-67-1 ]

Reference： [1]Bioscience, Biotechnology and Biochemistry,2004,vol. 68,p. 170 - 174

4
[ 79538-03-7 ]
(2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R,3R)-2,2-dimethyl-3-((1Z)-1-propenyl)cyclopropanecarboxylate [ No CAS ]

Reference： [1]Bioscience, Biotechnology and Biochemistry,2004,vol. 68,p. 170 - 174

5
[ 79538-03-7 ]
cis-Z-(+) 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-cyclopropane carboxylic acid chloride [ No CAS ]
tefluthrin [ No CAS ]

Reference： [1]Patent: WO2002/6202,2002,A1 .Location in patent: Example 13

6
[ 79538-03-7 ]
methyl 1R-2,2-dimethyl-3-(1-propenyl)cyclopropane carboxylate [ No CAS ]
2,3,5,6-tetrafluoro-4-methylbenzyl 1R-2,2-dimethyl-3-(1-propenyl)cyclopropane carboxylate [ No CAS ]

Reference： [1]Patent: EP1203760,2002,A1 .Location in patent: Example 3
[2]Patent: EP1203760,2002,A1 .Location in patent: Example 4
[3]Patent: EP1203760,2002,A1 .Location in patent: Page column 15

7
[ 92339-07-6 ]
[ 79538-03-7 ]
[ 703-87-7 ]

Yield	Reaction Conditions	Operation in experiment
82 - 88%Chromat.; 4 - 11%Chromat.	With hydrogen;sponge cobalt catalyst in water-containing state; In toluene; at 160℃; under 3975.4 - 165017 Torr; for 0.5 - 1h;Product distribution / selectivity;	To a 1 liter autoclave, 300 ml of toluene, 25 g of a sponge cobalt catalyst in a water-containing state (in which the catalyst amount is 5 g) and 30 g of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol were charged and a gas phase was thoroughly purged with hydrogen, and thereafter the hydrogen pressure was set to 1.5 MPa at ordinary temperature (the pressure means gauge pressure hereinafter). The stirring and heating for the autoclave were started and the temperature thereof was kept to 160 C. When the temperature reached to 160 C., the pressure was 2.2 MPa. The reaction was continued for 1 hr. Then, the autoclave was cooled to room temperature. After the cooling, the pressure showed 1.0 MPa. At this time, the amount of absorbed hydrogen was 104 mol % based on 2,3,5,6-tetrafluorobenzene-1,4-dimethanol charged. Hydrogen inside a reactor was removed, and thereafter the reaction mixture was recovered and the catalyst was filtered. [0059] The reaction mixture was heated under reduced pressure to remove the solvent by distillation, and further by gradually decreasing the pressure, a fraction distilled at 665 Pas at a temperature of from 100 to 105 C. was recovered. The fraction was analyzed with nuclear magnetic resonance spectrum (NMR) analysis and gas chromatography-mass spectroscopy (GC-MS) to identify 98% 2,3,5,6-tetrafluoro-4-methyl-benzyl alcohol. [0060] Further, using the distilled 2,3,5,6-tetrafluoro-4-methyl-benzyl alcohol as an authentic sample, a part of the reaction mixture recovered in the above reaction was analyzed with the gas chromatography internal standard method. In result, the conversion of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol was 94%, the yield of 2,3,5,6-tetrafluoro-4-methyl-benzyl alcohol was 88% (on the basis of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol), and the yield of 2,3,5,6-terafluoro-p-xylene was 4% (on the basis of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol).Example 5 [0068] To a 1 liter autoclave, 600 ml of toluene, 30 g of a sponge cobalt catalyst in a water-containing state (in which the catalyst amount is 6 g) and 60 g of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol were charged and gas phase was thoroughly purged with nitrogen. The stirring and heating for the autoclave were started and the temperature thereof was kept to 160 C. The pressure at this time was 0.28 MPa. Hydrogen was charged to the autoclave to increase the pressure to 0.53 MPa. Then, hydrogen was further fed to the autoclave to keep the pressure at 0.53 MPa, and when the hydrogen absorbing amount reached to 130 mol % based on 2,3,5,6-tetrafluorobenzene-1,4-dimethanol charged while watching the hydrogen flow rate, the reaction was stopped. The reaction required 30 minutes. [0069] Then, the autoclave was cooled to room temperature, gases inside the reactor were removed, and thereafter the reaction mixture was recovered and the catalyst was filtered. [0070] The resulting reaction mixture was analyzed with the gas chromatography internal standard method. In result, the conversion of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol was 99.5%, the yield of 2,3,5,6-tetrafluoro-4-methyl-benzyl alcohol was 82% (on the basis of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol), and the yield of 2,3,5,6-tetrafluoro-p-xylene was 11% (on the basis of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol).
58%Chromat.; 14%Chromat.	With hydrogen;rhenium oxide-alumina catalyst; In 1,4-dioxane; at 220℃; under 36003.6 Torr; for 5h;Product distribution / selectivity;	Example 4 To a 100 ml autoclave, 30 ml of 1,4-dioxane, 1.5 g of a supported rhenium oxide-alumina catalyst and 3.0 g of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol were charged and a gas phase was thoroughly purged with hydrogen, and thereafter the hydrogen pressure was set to 3 MPa at ordinary temperature.The stirring and heating for the autoclave were started and the temperature thereof was kept to 220 C. When the temperature reached to 220 C., the pressure was 4.8 MPa. The reaction continued for 5 hr. Then, the autoclave was cooled to room temperature and the pressure after the cooling showed 2.6 MPa. At this time, the amount of absorbed hydrogen was 116 mol % based on 2,3,5,6-tetrafluorobenzene-1,4-dimethanol charged.hydrogen inside a reactor was removed, and thereafter the reaction mixture was recovered and the catalyst was filtered.The resulting reaction mixture was analyzed with the gas chromatography internal standard method.In result, the conversion of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol was 83%, the yield of 2,3,5,6-tetrafluoro-4-methyl-benzyl alcohol was 58% (on the basis of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol), and the yield of 2,3,5,6-terafluoro-p-xylene was 14% (on the basis of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol).
40%Chromat.; 7%Chromat.	With hydrogen;sponge cobalt catalyst in a water-containing state; In 1,4-dioxane; at 160℃; under 3750.38 Torr; for 4h;Product distribution / selectivity;	Example 2 To a 100 ml autoclave, 30 ml of 1,4-dioxane, 2.5 g of a sponge cobalt catalyst in a water-containing state (in which the catalyst amount is 0.5 g) and 3.0 g of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol were charged and a gas phase was thoroughly purged with hydrogen, and thereafter the hydrogen pressure was set to 0.3 MPa at ordinary temperature.The stirring and heating for the autoclave were started and the temperature thereof was kept to 160 C. When the temperature reached to 160 C., the pressure was 0.5 MPa. hydrogen was fed to the autoclave to keep a pressure at 0.5 MPa, and when the hydrogen absorbing amount reached to 145 mol % based on 2,3,5,6-tetrafluorobenzene-1,4-dimethanol charged while watching the hydrogen flow rate, the reaction was stopped.The reaction required 4 hr. Then, the autoclave was cooled to room temperature.hydrogen inside a reactor was removed, and thereafter the reaction mixture was recovered and the catalyst was filtered. The resulting reaction mixture was analyzed with the gas chromatography internal standard method.In result, the conversion of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol was 69%, the yield of 2,3,5,6-tetrafluoro-4-methyl-benzyl alcohol was 40% (on the basis of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol), and the yield of 2,3,5,6-terafluoro-p-xylene was 7% (on the basis of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol).

37%Chromat.; 6%Chromat.

With hydrogen;palladium on activated charcoal; In 1,4-dioxane; at 220℃; under 67506.8 Torr; for 12h;Product distribution / selectivity;

Example 3 To a 100 ml autoclave, 30 ml of 1,4-dioxane, 3.0 g of a supported palladium-carbon catalyst and 3.0 g of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol were charged and a gas phase was thoroughly purged with hydrogen, and thereafter the hydrogen pressure was set to 5 MPa at ordinary temperature.The stirring and heating for the autoclave were started and the temperature thereof was kept to 220 C. When the temperature reached to 220 C., the pressure was 9 MPa. The reaction continued for 12 hr.Then, the autoclave was cooled to room temperature and the pressure after the cooling showed 4.7 MPa. At this time, the amount of absorbed hydrogen was 82 mol % based on 2,3,5,6-tetrafluorobenzene-1,4-dimethanol charged. hydrogen inside a reactor was removed, and thereafter the reaction mixture was recovered and the catalyst was filtered.The resulting reaction mixture was analyzed with the gas chromatography internal standard method.In result, the conversion of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol was 56%, the yield of 2,3,5,6-tetrafluoro-4-methyl-benzyl alcohol was 37% (on the basis of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol), and the yield of 2,3,5,6-terafluoro-p-xylene was 6% (on the basis of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol).

Reference： [1]Patent: US2004/10167,2004,A1 .Location in patent: Page 3-5
[2]Patent: US2004/10167,2004,A1 .Location in patent: Page 4
[3]Patent: US2004/10167,2004,A1 .Location in patent: Page 4
[4]Patent: US2004/10167,2004,A1 .Location in patent: Page 4

8
[ 79538-03-7 ]
[ 40447-55-0 ]
4-methyl-2,3,5,6-tetrafluorobenzyl 2,2-dimethyl-3-(1-propenyl)cyclopropanecarboxylate [ No CAS ]

Reference： [1]Patent: JP2005/82501,2005,A .Location in patent: Page/Page column 9; 10
[2]Patent: JP2005/82501,2005,A .Location in patent: Page/Page column 9; 10

9
[ 79538-03-7 ]
methyl 1R-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate [ No CAS ]
[ 223419-26-9 ]

Yield	Reaction Conditions	Operation in experiment
77.4%	With lithium methanolate; In n-heptane;	Internal Standard: biphenyl Example 4 Into a 100 ml round-bottomed flask were added 6.57 g of methyl 1R-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate (0.034 mol), 20 g of n-heptane and 0.049 g (0.0013 mol) of lithium methoxide, and 5.0 g (0.026 mol) of <strong>[79538-03-7]2,3,5,6-tetrafluoro-4-methylbenzyl alcohol</strong> dissolved by heating in 10 g of n-heptane was added thereto over 2 hours at 105 to 106 C., while removing a distillate fraction at the temperature. The reaction mixture was further heated at the temperature for 8 hours, while n-heptane was added dropwise to remove distillate fraction at the temperature. Thereafter the reaction mixture was concentrated to give crude 10.1 g of 2,3,5,6tetrafluoro-4-methylbenzyl 1R-trans-2,2-dimethyl-3-(2-methyl-1propenyl)cyclopropanecarboxylate. Gas-chromatography analysis of the crude product showed that content of the desired product was found to be 77.4% and the yield of the desired product was found to be 88.7%.

Reference： [1]Patent: US2002/52525,2002,A1

Yield	Reaction Conditions	Operation in experiment
		...ein R6 represents a methyl or ethyl group substituted with at least one member selected from the aryl group which may be substituted as defined above, a cyano group; or the alkynyl group, include, for example, aralkyl alcohols such as: benzyl alcohol, 2-methyl-3-phenylbenzyl alcohol, 2,3,5,6-tetrafluorobenzyl alcohol, 2,3,5,6-tetrafluoro-4-methylbenzyl alcohol, 2,3,5,6-tetrafluoro-4-methoxybenzyl alcohol, 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl alcohol, 2,3,5,6-tetrafluoro-4-propargylbenzyl alcohol, 2,3,5,6-tetrafluoro-4-(difluoromethyl)benzyl alcohol, 2,3,5,6-tetrafluoro-4-(difluoromethoxy)benzyl alcohol, 2,3,5,6-tetrafluoro-4-(2,2,2-trifluoroacetyloxy)methyl-benzyl alcohol, 4-(trifluoromethyl)benzyl alcohol, ...
		Specific insecticidally useful compounds according to the invention include the esters derived from each of: 4-methyl-2,3,5,6-tetrafluorobenzyl alcohol pentafluorobenzyl alcohol 4-allyl-2,3,5,6-tetrafluorobenzyl alcohol 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl alcohol 3-phenoxybenzyl alcohol α-cyano-3-phenoxybenzyl alcohol 6-phenoxypyrid-2-ylmethanol 1-cyano-1-(6-phenoxypyrid-2-yl)methanol 3-(4-chlorophenoxybenzyl) alcohol ...

11
[ 79538-03-7 ]
(2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate [ No CAS ]
[ 188023-87-2 ]
(2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R)-trans-3-formyl-2,2-dimethyl-cyclopropanecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; dimethylsulfide; p-toluenesulfonic acid monohydrate; In tetrahydrofuran; methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water; ethyl acetate; acetone;	Production Example 1 2.06 Grams of (1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid chloride was added to a mixture of 1.78 g of (2,3,5,6-tetrafluoro-4-methylphenyl)methanol, 0.87 g of pyridine and 20 ml of tetrahydrofuran under ice-cooling. The resulting mixture was stirred at room temperature for 8 hours. The reaction mixture was poured into about 100 ml of ice water and extracted twice with 100 ml of ethyl acetate. The combined ethyl acetate layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=20/1) to obtain 2.75 g (yield: 87%) of (2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate. A mixture of 1.27 g of (2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate, 20 ml of methanol and 20 ml of ethyl acetate was cooled to -78 C. Oxygen-containing ozone was bubbled into the mixture while stirring until the reaction mixture was colored blue. Then, nitrogen gas was bubbled into the blue reaction mixture to remove the excess ozone. Thereafter, 5 ml of dimethyl sulfide was added thereto. The resulting mixture was heated to room temperature. The reaction mixture, after having been allowed to stand for one day, was concentrated under reduced pressure. 20 Milliliters of acetone, 2 ml of water and 0.2 g of p-toluenesulfonic acid monohydrate were added to the resultant residue. The resulting reaction mixture, after having been allowed to stand at room temperature for 2 hours, was poured into water and extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=10/1) to obtain 0.98 g (yield: 82%) of (2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R)-trans-3-formyl-2,2-dimethyl-cyclopropanecarboxylate, m.p. 43.2 C.

Reference： [1]Patent: US6034128,2000,A

12
[ 79538-03-7 ]
[ 38078-09-0 ]
4-(fluoromethyl)-2,3,5,6-tetrafluorotoluene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	Preparation of 4-(fluoromethyl)-2,3,5,6-tetrafluorotoluene A stirred solution of <strong>[79538-03-7]4-methyl-2,3,5,6-tetrafluorobenzyl alcohol</strong> (3g, prepared according to the method described in UK patent application No. 2066810) in dichloromethane (20 cm3) maintained under an atmosphere of nitrogen was cooled to -10C and N,N-diethylaminosulphurtrifluoride (3.0 cm3) was added dropwise. The temperature of the mixture was maintained below 0C during the addition and for a further 30 minutes. The mixture was allowed to warm to the ambient temperature (ca 25C) and stirred for 3 hours before being poured into water. The products were extracted into dichloromethane. The organic layers were combined and washed with sodium bicarbonate solution, then dried over anhydrous magnesium sulphate. Evaporation of the solvent under reduced pressure gave an oil which was purified by flash column chromatography on a silica gel support, eluding with dichloromethane. Evaporation of the eluent gave a liquid which was further purified by short path distillation at a bulb temperature of 50C under reduced pressure (0.5 mbar) to give 4-(fluoromethyl)-2,3,5,6-tetrafluorotoluene (1g) as a colourless liquid. 1H NMR (CDCl3): 5.5 (2H,d); 2.3 (3H,s) 19F NMR (CDCl3): -211 (t); -144 (d).

Reference： [1]Patent: EP302626,1989,A3

13
[ 79538-03-7 ]
[ 188023-87-2 ]
profluthrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With pyridine; In tetrahydrofuran; ice-water; ethyl acetate;	Production Example 1 To a mixture solution of 1.78 g of (2,3,5,6-tetrafluoro-4-methylphenyl)methanol, 0.87 g of pyridine and 20 ml of tetrahydrofuran, 2.06 g of (1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic chloride was added under ice-cooling and the mixture was stirred for 8 hours at room temperature. The reaction mixture was poured into about 100 ml of ice-water and extracted with each 100 ml of ethyl acetate twice. The combined ethyl acetate was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a crude product, which was subjected to silica gel column chromatography (eluent: hexane/ethyl acetate=20/1) to give 2.75 g of (2,3,5,6-tetrafluoro-4-methylphenyl)methyl(1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate (yield 87%).

Reference： [1]Patent: US6225495,2001,B1

14
[ 79538-03-7 ]
[ 393870-46-7 ]
tefluthrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96.5%	With pyridine; In toluene; at 35 - 95℃; for 2h;Product distribution / selectivity;	Step iii. Preparation of Tefluthrin; Cis-((Z)-2-chloro-3,3,3-trifluoro-prop-1-enyl)-2,2-dimethylcyclopropane acyl chloride (257 g was charged to a four-neck reactor fitted with an dispersion agitator. Toluene (257 g, molten <strong>[79538-03-7]2,3,5,6-tetrafluoro-4-methylbenzyl alcohol</strong> (188.1 g and suitably added pyridine (51 g were charged together into the dropping funnel. The alcohol solution was dropped to the acyl chloride. The temperature was kept at 35-45 C. during the addition. On completion of the addition, the temperature of the reaction mass was raised to 95 C. and held for 2 hours. The mixture was cooled to 60 C. and washed with water to dissolve the salts and then distilled. The reaction yielded 410.3 g of tefluthrin. Analysis showed that the amount of tefluthrin was 95.5 wt % and the reaction yield was 96.5%.; Example 8; Preparation (2) of Tefluthrin [2,3,5,6-tetrafluoro-4-benzyl cis-((Z)-2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane carboxylate]; Methanol (250 ml) and sodium borohydride (20 g were added into a 1000 ml enamel autoclave. Tetrafluorodimethylterephthalate (133 g was slowly added to the reactor while controlling the temperature at 50 C. The mixture was stirred under these conditions for 5 hours and sampled for GC periodically. After GC revealed that the diester had disappeared, 30% aqueous hydrochloric acid (20 ml) was added into the mixture and the resulting mixture was then extracted with tetrachloromethane (250 ml). The tetrachloromethane was removed under reduced pressure and then 48% aqueous hydrobromic acid (122.3 g and toluene (300 ml) were added to the reaction mixture and then the mixture was heated to 95 C. The mixture was refluxed at 95-100 C. for 30 minutes and the toluene water azeotrope was collected. After the reaction was continued for 5.5 hours, the mixture was cooled to 55 C., washed once with 5% aqueous sodium acetate solution and from which toluene as the solvent was removed. Methanol (450 g, water (7.5 g, and 5% palladium/carbon catalyst (1.2 g 100% wt.) were charged to the residue. The lid was sealed and the autoclave was initially purged with nitrogen to remove residual oxygen (to nearly zero) and then pressurized to 2.5 bar with hydrogen. The reaction temperature was controlled at about 50 C. The reaction was continued until the consumption of hydrogen ceased. The residual pressure was released and the autoclave purged with nitrogen. The spent catalyst and inorganic salts were removed by filtration. The solvent was distilled from the filtrate. And then toluene (150 ml) and pyridine (28.8 g were added to the residue. Cis-((Z)-2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane formyl chloride (85.8 g was dropped slowly into the mixture when the temperature was heated to 35-45 C. After completion of the addition, the temperature of the reaction mass was raised to 75-90 C. and held for 2 hours. The mixture was cooled to 60 C. and washed with water to dissolve the salts and then distilled to remove solvent. The reaction yielded 71.1 g of tefluthrin, and analysis showed that the amount of tefluthrin was 94.9% by weight and the overall reaction yield from tetrafluorodimethylterephthalate was 64.1%.

Reference： [1]Patent: US2007/55075,2007,A1 .Location in patent: Page/Page column 4-5

15
[ 99705-46-1 ]
[ 79538-03-7 ]

Yield	Reaction Conditions	Operation in experiment
89.4%	With hydrogen; magnesium oxide;5%-palladium/activated carbon; In methanol; water; at 50℃; under 1875.19 Torr; for 1 - 1.5h;Product distribution / selectivity;	Step ii. Preparation of 4-methyl-2,3,5,6-tetrafluorobenzyl alcohol; The following procedures were carried out in a 1 litre glass autoclave (working volume 350-500 mls) fitted with a dispersion agitator (1000 rpm). H2 gas was fed through a dip-pipe via a Buchi gas controller (Type 6002). The increase/decrease of the temperature is controlled by a Jelabo FP40 external heating/cooling bath. Methanol (362 g, water (6 g, 2,3,5,6-tetrafluoro-4-(bromomethyl)benzyl alcohol (95.1 g 100% wt.), MgO (18.1 g and 5% palladium/carbon catalyst (0.8 g, 100 wt %; Type 58, provided by Johnson Matthey) were charged to the autoclave. The lid was sealed and the autoclave was initially purged with nitrogen to remove residual oxygen (nearly 0), then pressurized to 2.5 bar with hydrogen, and stirred. The pressure was maintained at 2.5 bar by the Buchi controller. The reaction temperature was controlled at 50 C. throughout the reaction by means of the external heating/cooling bath. The reaction was continued until the consumption of hydrogen ceased (typically 60 to 90 minutes). The residual pressure was released and the autoclave purged with nitrogen. The contents of the autoclave were discharged, followed by a small methanol (30 g wash. The spent catalyst and inorganic salts were removed and recovered by filtration. The filter cake was washed with a small amount of methanol (2×30 g. The filtrates and filter-cake washes were combined. On analysis, the reaction had produced 60.4 g of 2,3,5,6-tetrafluoro-4-methylbenzyl alcohol with a yield of 89.4%.
	With hydrogen;5%-palladium/activated carbon; In methanol; water; at 50℃; under 1875.19 Torr;Product distribution / selectivity;	Example 8; Preparation (2) of Tefluthrin [2,3,5,6-tetrafluoro-4-benzyl cis-((Z)-2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane carboxylate]; Methanol (250 ml) and sodium borohydride (20 g were added into a 1000 ml enamel autoclave. Tetrafluorodimethylterephthalate (133 g was slowly added to the reactor while controlling the temperature at 50 C. The mixture was stirred under these conditions for 5 hours and sampled for GC periodically. After GC revealed that the diester had disappeared, 30% aqueous hydrochloric acid (20 ml) was added into the mixture and the resulting mixture was then extracted with tetrachloromethane (250 ml). The tetrachloromethane was removed under reduced pressure and then 48% aqueous hydrobromic acid (122.3 g and toluene (300 ml) were added to the reaction mixture and then the mixture was heated to 95 C. The mixture was refluxed at 95-100 C. for 30 minutes and the toluene water azeotrope was collected. After the reaction was continued for 5.5 hours, the mixture was cooled to 55 C., washed once with 5% aqueous sodium acetate solution and from which toluene as the solvent was removed. Methanol (450 g, water (7.5 g, and 5% palladium/carbon catalyst (1.2 g 100% wt.) were charged to the residue. The lid was sealed and the autoclave was initially purged with nitrogen to remove residual oxygen (to nearly zero) and then pressurized to 2.5 bar with hydrogen. The reaction temperature was controlled at about 50 C. The reaction was continued until the consumption of hydrogen ceased. The residual pressure was released and the autoclave purged with nitrogen. The spent catalyst and inorganic salts were removed by filtration. The solvent was distilled from the filtrate. And then toluene (150 ml) and pyridine (28.8 g were added to the residue. Cis-((Z)-2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane formyl chloride (85.8 g was dropped slowly into the mixture when the temperature was heated to 35-45 C. After completion of the addition, the temperature of the reaction mass was raised to 75-90 C. and held for 2 hours. The mixture was cooled to 60 C. and washed with water to dissolve the salts and then distilled to remove solvent. The reaction yielded 71.1 g of tefluthrin, and analysis showed that the amount of tefluthrin was 94.9% by weight and the overall reaction yield from tetrafluorodimethylterephthalate was 64.1%.

Reference： [1]Patent: US2007/55075,2007,A1 .Location in patent: Page/Page column 4
[2]Patent: US2007/55075,2007,A1 .Location in patent: Page/Page column 4-5

16
[ 79538-03-7 ]
[ 1052115-15-7 ]
4-methyl-2,3,5,6-tetrafluorobenzyl (1R)-trans-3-((Z)-2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylate [ No CAS ]
4-methyl-2,3,5,6-tetrafluorobenzyl (1R)-trans-3-((E)-2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dicyclohexyl-carbodiimide;dmap; In dichloromethane; at 20℃; for 3h;	Under a nitrogen atmosphere, 0.59 g of N, N- dicyclohexyl carbodiimide was added to a mixture of 0.55 g of 4-methyl-2, 3, 5, 6-tetrafluorobenzyl alcohol, 0.51 g of (IR) -trans-3- (2-cyano-l-propenyl) -2,2- dimethylcyclopropanecarboxylic acid, 0.10 g of 4- dimethylaminopyridine and 7 ml of anhydrous dichloromethane, and the mixture was stirred at room temperature for 3 hours. Thereafter, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 0.72 g of 4-methyl-2, 3, 5, 6- tetrafluorobenzyl (IR) -trans-3- (2-cyano-l-propenyl) -2, 2- dimethylcyclopropanecarboxylate represented by the <n="41"/>following formula:(ratio of isomers regarding double bond: Z/E = about 2/1) , (hereinafter, referred to as the present compound (I)). 1H-NMR (CDCl3, TMS) δ (ppm) : 1.21 (s, 3H, Z+E isomers), 1.32 (s, 3H, Z+E isomers), 1.71 (t, IH, Z+E isomers), 1.95(s, 3H, Z+E isomers), 2.19 (m, 1/3H, E isomer), 2.29 (s, 3H, Z+E isomers), 2.45 (m, 2/3H, Z isomer), 5.24 (s, 2H, Z+E isomers), 5.78 (d, 2/3H, Z isomer), 6.00 (d, 1/3H, E isomer)

Reference： [1]Patent: WO2008/108376,2008,A1 .Location in patent: Page/Page column 39-40

17
[ 99705-45-0 ]
[ 79538-03-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;5%-palladium/activated carbon; In water; butan-1-ol; at 100℃; for 16h;Inert atmosphere;Product distribution / selectivity;	Into a 100 mL flask equipped with a reflux condenser, 1.2 g of 5% by weight palladium/carbon (containing water of 50% by weight), 6.1 g of 4-chloromethyl-2,3,5,6-tetrafluorobenzyl alcohol obtained in Example 18, and 30 g of n-butanol were charged. The substitution of the gas phase part inside the flask with nitrogen was conducted followed by substituting with hydrogen, and then a 1L-volume rubber balloon filled with hydrogen was equipped to the flask. The mixture was heated to 100C to conduct the reaction for 16 hours at the same temperature while stirring. The reaction mixture was cooled to room temperature. The catalyst was removed by filtration, and the catalyst was washed with 10 g of ethyl acetate. The filtrate and the wash liquid were mixed to concentrate to obtain white crystals of 4.7 g of white crystals of 4-methyl-2,3,5,6-tetrafluorobenzyl alcohol. The crystals were analyzed by gas chromatography area percentage method to find out that the purity thereof was 98%. Yield: 90%.

Reference： [1]Patent: EP2123624,2009,A1 .Location in patent: Page/Page column 13

18
[ 79538-03-7 ]
C₉H₁₀ClF₃O₂ [ No CAS ]
tefluthrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	zirconium(IV) chloride; In xylene; at 140℃; for 3h;Product distribution / selectivity;	Reaction of PP890 acid (VIII) and TFX-OH (IX) for 3 hours at 140 0C in the presence of a small amount of zirconium tetrachloride (1 mol%) gave very little conversion (2 %). Addition of more catalyst (10 mol %) resulted in clean and rapid conversion to the desired tefluthrin product (VII).The identity of the product was confirmed by GCMS and NMR comparison with authentic material .

Reference： [1]Patent: WO2009/138373,2009,A2 .Location in patent: Page/Page column 15

19
[ 289891-56-1 ]
[ 79538-03-7 ]

Reference： [1]Journal of Fluorine Chemistry,2009,vol. 130,p. 938 - 941

20
[ 3217-47-8 ]
[ 79538-03-7 ]
[ 703-87-7 ]
[ 92339-07-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;cobalt R400; In toluene; at 120 - 150℃; under 3750.38 - 5625.56 Torr; for 10.5h;Autoclave;Product distribution / selectivity;	In a 100 ml autoclave, 6.0 g (29.1 mmol) of 2,3,5,6-tetrafluorobenzene-1,4-dicarbaldehyde, 24.0 g of toluene and 0.6 g of a sponge cobalt catalyst (R-400 manufactured by Nikko Rica Corporation) having been separately subjected to methanol replacement and toluene replacement in advance were placed.First, the autoclave was purged with nitrogen at room temperature and then purged with hydrogen. Subsequently, the temperature of the autoclave was raised to 120 C., then hydrogen was fed to the autoclave with maintaining the pressure at 0.5 MPa, and the reaction was carried out at a temperature of 120 C. for 5 hours. The ratio of absorption of hydrogen at this time was 63%. The temperature of the autoclave was further raised up to 150 C. over a period of 20 minutes, then hydrogen was fed to the autoclave with maintaining the pressure at 0.75 MPa, and the reaction was further, carried out at a temperature of 150 C. for 5 hours and 10 minutes. The ratio of absorption of hydrogen through the whole reaction was 102%. Then, feeding of hydrogen was terminated, and the autoclave was cooled to room temperature. Subsequently, the catalyst was filtered out, and the reaction liquid was taken out.A small amount of a sample was withdrawn and subjected to GC analysis. As a result of the analysis, a peak of the 2, 3, 5, 6-tetrafluorobenzene-1,4-dicarbaldehyde as a raw material was not more than the limit of detection, the formation ratio of 2,3,5,6-tetrafluoro-4-methylbenzyl alcohol was 80.8%, the formation ratio of 1,4-dimethyl-2,3,5,6-tetrafluorobenzene was 8.6%, and the formation ratio of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol was 6.9%.

Reference： [1]Patent: US2010/145106,2010,A1 .Location in patent: Page/Page column 5

21
[ 79538-03-7 ]
trans-3-(2-chloro-vinyl)-2,2-dimethylcyclopropane carboxylic acid [ No CAS ]
trans-(2,3,5,6-tetrafluoro-4-methyl-benzyl)-3-(2-chlorovinyl)-2,2-dimethylcyclopropane-carboxylate [ No CAS ]

Reference： [1]Journal of Agricultural and Food Chemistry,2011,vol. 59,p. 1171 - 1177

22
[ 79538-03-7 ]
C₈H₁₁ClO₂ [ No CAS ]
C₁₆H₁₅ClF₄O₂ [ No CAS ]

Reference： [1]Journal of Agricultural and Food Chemistry,2011,vol. 59,p. 1171 - 1177

23
[ 79538-03-7 ]
[ 22573-51-9 ]
[ 1462940-80-2 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide; In acetonitrile; at 20℃; for 10h;	General procedure: A solution of acid 2 (2 mmol) and substituted tetrafluorobenzyl alcohol(2 mmol) in CH3CN (10 mL) was stirred at room temperature, to whicha catalytic amount of DMAP (0.1 g)and dicyclohexylcarbodiimide (2.4 mmol) was added after the solid in thesolution has absolutely dissolved. And then the mixture was stirred for another10 h. The precipitate of DCU was removed by filtration through a Buchnerfunnel, and the filtrate was washed with two 20 mL portions of saturated sodiumcarbonate solution and three 20 mL portions of saturated sodium chloridesolution. The organic layer was dried over anhydrous sodium sulfate andconcentrated with a rotary evaporator, and theresidue was purified by silica gel column-chromatography(ethyl acetate/petroleum ether) to give thedesired products 3.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2734 - 2736

24
[ 79538-03-7 ]
[ 1610701-00-2 ]
[ 1462941-07-6 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide; In acetonitrile; at 20℃; for 10h;	General procedure: A solution of acid 2 (2 mmol) and substituted tetrafluorobenzyl alcohol(2 mmol) in CH3CN (10 mL) was stirred at room temperature, to whicha catalytic amount of DMAP (0.1 g)and dicyclohexylcarbodiimide (2.4 mmol) was added after the solid in thesolution has absolutely dissolved. And then the mixture was stirred for another10 h. The precipitate of DCU was removed by filtration through a Buchnerfunnel, and the filtrate was washed with two 20 mL portions of saturated sodiumcarbonate solution and three 20 mL portions of saturated sodium chloridesolution. The organic layer was dried over anhydrous sodium sulfate andconcentrated with a rotary evaporator, and theresidue was purified by silica gel column-chromatography(ethyl acetate/petroleum ether) to give thedesired products 3.
	With dmap; dicyclohexyl-carbodiimide; In acetonitrile; at 20℃; for 10h;	General procedure: A solution of 1 (8 mmol) in THF/H2O (40 mL THF, 10 mL H2O) was cooled to 0oC, to which lithium hydroxide (9.6 mmol) and hydrogen peroxide (19.2 mmol) was added. After 12 hours reaction, a small amount of sodium sulfite was added in to remove the excess hydrogen peroxide. Then 2 N HCl was added dropwise to adjust the pH value to 2-3. The reaction mixture was extracted with ether (2×30 mL). The combined organic layers were washed with brine (50 mL), concentrated under vacuum, and puried by silica gel chromatography to get pure acids 2 and auxiliary sultam. A solution of acid 2 (2 mmol) and substituted tetrafluorobenzyl alcohol (2 mmol) in CH3CN (10 mL) was stirred at room temperature, to which a catalytic amount of DMAP (0.1 g) and dicyclohexylcarbodiimide (2.4 mmol) was added after the solid in the solution has absolutely dissolved. And then the mixture was stirred for another 10 h. The precipitate of DCU was removed by filtration through a Buchner funnel, and the filtrate was washed with two 20 mL portions of saturated sodium carbonate solution and three 20 mL portions of saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate and concentrated with a rotary evaporator, and the residue was purified by silica gel column-chromatography (ethyl acetate/petroleum ether) to give the desired products 3. Their physico-chemical properties and the spectra data are as follows:

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2734 - 2736
[2]Bioorganic and Medicinal Chemistry Letters,2015,vol. 24,p. 2734 - 2736

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[ CAS No. 79538-03-7 ] 2,3,5,6-Tetrafluoro-4-methylbenzyl Alcohol

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[ 79538-03-7 ] Synthesis Path-Downstream 1~24

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