[ CAS No. 140690-56-8 ] {[proInfo.proName]}

Name: 140690-56-8|1-(Bromomethyl)-2,4-bis(trifluoromethyl)benzene|98%
Brand: Ambeed
SKU: A574304
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Quality Control of [ 140690-56-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 140690-56-8 ]

CAS No. :	140690-56-8	MDL No. :	MFCD00010306
Formula :	C₉H₅BrF₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SWFFFUJOWAJJCH-UHFFFAOYSA-N
M.W :	307.03	Pubchem ID :	518871
Synonyms :

Safety of [ 140690-56-8 ]

Signal Word:	Danger	Class:	8,3
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	2920
Hazard Statements:	H225-H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 140690-56-8 ]

* 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 [ 140690-56-8 ]

[ 140690-56-8 ] Synthesis Path-Downstream 1~80

1
[ 140690-56-8 ]
[ 736155-95-6 ]
8-(2,4-bis-trifluoromethyl-benzyloxy)-4-methyl-1,2,5,6-tetrahydro-pyrido[1,2-a]quinolin-3-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 3546 - 3560

2
[ 121-33-5 ]
[ 140690-56-8 ]
[ 796844-14-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 2h;	Reference Example 2 4-[2,4-bis(trifluoromethyl)benzyl]oxy}-3-methoxybenzaldehyde; [Show Image] To a solution (25 mL) of vanillin (2.13 g) in anhydrous DMF were added <strong>[140690-56-8]2,4-bis(trifluoromethyl)benzyl bromide</strong> (4.72 g) and potassium carbonate (2.13 g), and the mixture was stirred at room temperature for 2 hr. Water was added to the reaction mixture, and the precipitated solid was collected by filtration. The solid was washed with water, and dried to give the title compound as a white solid (yield: 5.2 g, 98%). 1H-NMR (DMSO-d6, 400 MHz):delta3.87 (3H, s), 5.46 (2H, s), 7.28 (1H, d, J = 8.3 Hz), 7.47 (1H, d, J = 1.7 Hz), 7.57 (1H, dd, J = 8.3, 1.7 Hz), 8.04 (1H, d, J = 8.1 Hz), 8.12 (1H, s), 8.19 (1H, d, J = 8.3 Hz), 9.87 (1H, s).
86%	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 15h;	To a flask was added 1-bromomethyl-2,4-bis-trifluoromethyl-benzene (2.27 g, 7.39 mmol), vanillin (1.12 g, 1 equiv), DMF (23 mL) and fine mesh K2CO3 (5.11 g, 37 mmol). The reaction slurry was stirred at 70 0C for 15 h. The reaction solution was diluted with EtOAc (120 mL), filtered through a Buchner funnel, washed with sat NH4CI (50 mL x 2), dried over Na2SO4, filtered, and concentrated. The crude material was chromatographed (SiO2, Hex/EtOAc: 100:0 to 70:30) to yield intermediate product (2.79 g, 86%). 1H NMR (400 MHz, CDCI3) delta 9.88 (s, 1H), 7.97 (d, J = 8 Hz, 1H), 7.96 (s, 1H), 7.85 (d, J = 8 Hz, 1H), 7.48 (s, 1 H), 7.42 (d, J = 8 Hz, 1 H), 6.93 (d, J = 8 Hz, 1H), 5.48 (s, 2H), 3.99 (s, 3H); MS(ESI) 379 (MH+).
86%	With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 80℃; for 19h;Product distribution / selectivity;	Into a 250 mL round-bottomed flask was weighed 518 mg (3.41 mmol) of vanillin, 1.0 g (3.26 mmol) of 2, 4-bis-trifluoromethyl benzyl bromide, 500 mg of K2CO3, 5 mL of acetonitrile, and 2 mL of DMF. The resulting suspension was stirred under nitrogen at 80 C for 19 h. The reaction was then poured into a separatory funnel with ethyl acetate and water. The ethyl acetate was separated, washed with brine, dried (MgS04), and concentrated in vacuo. The residue was purified by silica gel flash chromatography (Jones Flashmaster, 50 g Si02, gradient elution from 100% hexanes to 100% ethyl acetate over 30 minutes). Appropriate fractions were combined, concentrated, and dried under high vacuum to afford the product as a colorless solid, yield : 1.06 g (86%).'H NMR (400 MHz, CDCI3) 8 : 9.88 (s, 1H), 7.97 (d, J = 8 Hz, 1 H), 7.96 (s, 1 H), 7.85 (d, J = 8 Hz, 1 H), 7.48 (s, 1 H), 7.42 (d, J = 8 Hz, 1H), 6.93 (d, J = 8 Hz, 1 H), 5.48 (s, 2H), 3.99 (s, 3H) ; MS (ESI) 379 (MH+).

85%	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 3h;	Compound 26 (3.07 g, 10 mmol) and vanillin (1.52 g, 10 mmol) were dissolved in DMF (10 ml), K2CO3 (2 g, 14 mmol) was added, and the mixture was stirred at 80C for 3 hours.After cooling to room temperature, the resulting mixture was extracted with ethyl acetate and water.The organic layer was separated, washed with brine, and dried over Na 2 SO 4.After spin-drying the solvent under reduced pressure, the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=7:1),The product 27 was obtained as a white solid (3.21 g, 8.50 mmol, 85%):
	With potassium carbonate; In acetone; at 65℃;	General procedure: 3-methoxy-4-hydroxy-benzaldehyde 1 and R1X (R1 = benzyl, alkyl, etc.) are dissolved inacetone solution, and potassium carbonate is added in two portions, and the mixture is stirred at 65 C for 4-12 hoursafter the addition. After the reaction is completed (TLC monitoring, UV development), the reaction solution is subjectedto suction filtration, and the filtrate is collected and concentrated by distillation under reduced pressure. The crude productis purified by silica gel column chromatography (petroleum ether/ethyl acetate) to give compound cc2. The yield is 70-90%.

Reference： [1]Patent: EP2450352,2012,A1 .Location in patent: Page/Page column 58
[2]Journal of Medicinal Chemistry,2004,vol. 47,p. 5593 - 5596
[3]Patent: WO2006/47269,2006,A2 .Location in patent: Page/Page column 41
[4]Patent: WO2005/72731,2005,A1 .Location in patent: Page/Page column 110
[5]ACS Medicinal Chemistry Letters,2019,vol. 10,p. 767 - 772
[6]Patent: CN111233661,2020,A .Location in patent: Paragraph 0167-0171
[7]Patent: EP3438108,2019,A1 .Location in patent: Paragraph 0062

3
[ 22446-38-4 ]
[ 140690-56-8 ]
ethyl 3-(2,4-bis(trifluoromethyl)benzyloxy)phenylacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 5h;	To a solution of Ethyl 3-hydroxyphenylacetate (3.22 g, 17.9 mmol) and potassium carbonate (2.92 g, 21.2 mmol) in dry N, N-Dimethylformamide (15 ml) was added 2,4- Bis(trifluoromethyl)benzyl bromide (5 g, 16.3 mmol). The reaction mixture was stirred at room temperature for 5 hours, quenched with water and concentrated in vaccuo. The crude residue was taken in ethyl acetate and washed with water and brine. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (hex: ether, 5: 1) to give the title compound.1H NMR (270 MHz, CDCl3): 1.2 (t, 3H); 3.6 (s, 2H); 4.1 (q, 2H); 5.3 (s, 2H); 6.8-7.0 (m, 3H); 7.3 (m, IH); 7.8 (d, IH); 7.9-8.0 (m, 2H).

Reference： [1]Patent: WO2007/146768,2007,A2 .Location in patent: Page/Page column 10

4
ethyl N-[(1-cyclohexyl-6-hydroxy-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)carbonyl]glycinate [ No CAS ]
[ 140690-56-8 ]
C₂₄H₂₅F₆N₃O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In ISOPROPYLAMIDE; at 100℃; for 3h;	A mixture of ethyl N-[(l-cyclohexyl-6-hydroxy-2,4-dioxo-l,2,3,4-tetrahydro-5- pyrimidinyl)carbonyl]glycinate (340 mg, 1.0 mmoles), pulv. potassium carbonate (750 mg, 5.35 mmoles) and <strong>[140690-56-8]2,4-bis(trifluoromethyl)benzyl bromide</strong> (375 uL, 2.0 mmoles) in dimethylacetamide (6 mL) was vigorously stirred at 1000C for 3 hours. The mixture was poured into 1 molar hydrochloric acid and extracted with ethyl acetate (x2). The combined organic solutions were washed with 1 molar hydrochloric acid and evaporated. The residue was purified by flash chromatography (10-50% ethyl acetate in hexane), the required fractions evaporated, dissolved in ethanol (5 mL) and 1 molar sodium hydroxide solution (3.0 mL) added. The mixture was stirred overnight, acidified and extracted with ethyl acetate (x2), the combined extracts washed with 1 molar hydrochloric acid, dried and evaporated. Recrystallization from acetic acid-water gave the <n="115"/>title compound (180 mg, 34%). IH NMR (400 MHz, DMSO-^6) delta ppm 13.11 (br. s., 1 H), 8.06 (s, 1 H), 7.98 (d, J=8.59 Hz, 1 H), 7.53 (d, J=8.34 Hz, 1 H), 5.23 (s, 2 H), 4.64 (t, J=12.00 Hz, 1 H), 4.13 (d, J=5.56 Hz, 2 H), 2.24 (q, 2 H), 1.78 (d, J=12.63 Hz, 2 H), 1.52 - 1.73 (m, 3 H), 1.28 (q, J=13.05 Hz, 2 H), 1.10 (q, 1 H).

Reference： [1]Patent: WO2007/150011,2007,A2 .Location in patent: Page/Page column 113-114

5
[ 1003884-02-3 ]
[ 140690-56-8 ]
(2S)-3-(4-{2-[(1α,5α,6α)-[3-(2,4-bistrifluoromethylbenzyl)-3-azabicyclo[3.1.0]hex-6-yl]-tert-butoxycarbonylamino]ethoxy}phenyl)-2-(4-tert-butylphenoxy)propionic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium carbonate; In acetonitrile; at 55℃; for 3h;	To a stirred solution of (2S)-3-(4-{2-[(lalpha,5alpha,6alpha)-(3-azabicyclo[3.1.0]hex-6-yl)-tert- butoxy-carbonylamino] ethoxy }phenyl)-2-(4-tert-butylphenoxy)propionic acid ethyl ester <n="178"/>(Intermediate 12; 0.500 g, 0.88 mmol) in dry acetonitrile (20 ml) was added anhydrous potassium carbonate (0.365 g, 2.65 mmol) and 2,4-bistrifluoromethylbenzyl bromide (0.298 g, 0.18 ml., 0.97 mmol) at room temperature and resulting reaction mixture was heated at 55 0C for 3 h. The solvent was removed under reduced pressure and the residue was partitioned between dichloromethane (50 ml) and water (20 ml). Organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to yield a crude product, which was purified by column chromatography over silica gel (100-200 mesh) using chloroform as an eluent to yield the title compound (0.590 g, 84%). MS: mlz 793 (M+l) 1HNMR (CDCl3, 200MHz): delta 1.17-1.25 (m, 12H), 1.45 (s, 9H), 1.72 (s, 2H), 2.49 (d, J= 8.3 Hz, 2H), 2.95 (s, IH), 3.06-3.17 (m, 4H), 3.56 (t, J= 5.2 Hz, 2H), 3.79 (s, 2H), 4.05 (t, J = 5.2 Hz, 2H), 4.18 (q, J= 7.1 Hz, 2H), 4.68 (t, J= 6.1 Hz, IH), 6.77 (t, J= 8.3 Hz, 4H), 7.18- 7.25 (m, 4H), 7.70-7.85 (m, 3H).

Reference： [1]Patent: WO2008/10238,2008,A2 .Location in patent: Page/Page column 176-177

6
[ 140690-56-8 ]
3-[4-(2,4-bis-trifluoromethyl-benzyloxy)-3-methoxy-phenyl]-2-cyano-N-[1,3,4]thiadiazol-2-yl-acrylamide [ No CAS ]