[ CAS No. 887267-47-2 ]

Name: 887267-47-2|2-Bromo-5-(trifluoromethoxy)aniline|98%
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CAS No. :	887267-47-2	MDL No. :	MFCD08458013
Formula :	C₇H₅BrF₃NO	Boiling Point :	234.7°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	256.02 g/mol	Pubchem ID :	26985111
Synonyms :

Safety of [ 887267-47-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302+H312+H332-H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 887267-47-2 ]

Upstream synthesis route of [ 887267-47-2 ]
Downstream synthetic route of [ 887267-47-2 ]

[ 887267-47-2 ] Synthesis Path-Upstream 1~2

1
[ 1535-73-5 ]
[ 887267-47-2 ]

Reference： [1] Patent: WO2009/3077, 2008, A1, . Location in patent: Page/Page column 140

2
[ 1535-73-5 ]
[ 116369-25-6 ]
[ 887267-47-2 ]

Reference： [1] Patent: WO2011/3684, 2011, A1, . Location in patent: Page/Page column 25

[ 887267-47-2 ] Synthesis Path-Downstream 1~26

1
[ 887267-47-2 ]
[ 24424-99-5 ]
C₁₂H₁₃BrF₃NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In water; tert-butyl alcohol; at 20℃; for 96h;	An aqueous solution of NaOH (10.2 g, 254 mmol in 20 mL water) was added to a solution of Preparation 67A in t-butanol (100 mL). Next, a solution of di- tert-butyldicarbonate (60.1 mL, 254 mmol) in t-butanol was added at room temperature and the resulting mixture was stirred for 4 days. The reaction mixture became a suspension and was filtered. The residue was washed with a small amount of water. The filtrate was concentrated to half its volume and then extracted with EtOAc (2 x 200 mL). The organic layer was washed with brine solution and dried over anhydrous Na2SO4. Removal of solvent in vacuo gave Preparation 67B (31.0 g) as a white solid.

Reference： [1]Patent: WO2009/3077,2008,A1 .Location in patent: Page/Page column 141

2
[ 1535-73-5 ]
[ 887267-47-2 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 12.667h;	A solution of NBS (20.1 g, 111.9 mmol) in DMF (40 mL) was added drop wise to a solution of 3-trifluoromethylaniline (20.0 g, 112.9 mmol) in DMF (80 mL) at room temperature over 40 minutes. The reaction mixture was stirred overnight.After 12 h, the reaction mixture was poured into water and extracted with EtOAc and the organic layer was dried over anhydrous Na2SO4. Concentration in vacuo gave 26 g of Preparation 67A. [00514] MS (ES): m/z = 256.2 [M+lf .

Reference： [1]Patent: WO2009/3077,2008,A1 .Location in patent: Page/Page column 140

3
[ 887267-47-2 ]
[ 4043-87-2 ]
[ 1186126-35-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4119 - 4121

4
[ 887267-47-2 ]
[ 140-88-5 ]
[ 1239461-98-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; tris-(o-tolyl)phosphine;palladium diacetate; In acetonitrile; at 120℃; for 18h;Inert atmosphere;	The aryl halide (e.g., 1.00 mmol), triethylamine (e.g., 2.00 mmol) and P(o-tol)3 (e.g., 0.30 mmol) were dissolved in acetonitrile (e.g., 0.5 M) in a glass pressure tube and nitrogen gas was bubbled through the solution via a gas dispersion tube for 10 minutes. Ethyl acrylate (e.g., 1.25 mmol) and palladium acetate (e.g., 0.10 mmol) were added to the reaction mixture and the tube was sealed and placed into an oil bath pre-heated to about 120 0C for about 18 h. The resulting solution was concentrated under vacuum and purified (e.g., silica gel column).The title compound was prepared from <strong>[887267-47-2]2-bromo-5-(trifluoromethoxy)aniline</strong> according to protocol M. Retention time (min) = 2.693, method [1], MS(ESI) 276.1 (M+Eta).

Reference： [1]Patent: WO2010/91310,2010,A1 .Location in patent: Page/Page column 136

5
[ 887267-47-2 ]
[ 63-91-2 ]
[ 1261061-24-8 ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 2531 - 2537
[2]Research on Chemical Intermediates,2014,vol. 40,p. 2157 - 2164

6
[ 1535-73-5 ]
[ 116369-25-6 ]
[ 887267-47-2 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; In toluene; at 20℃; for 2h;	The title compound was prepared according to procedures similar to those described in Example 1 starting from 2-bromo-5-trifluoromethoxy-aniline, which was obtained as follows:A solution of 3-trifluoromethoxy-aniline (1.77 g) in toluene (20 ml) was treated with Lambda/-bromosuccinimide (1.87 g) at ambient temperature and the reaction mixture was stirred for 2 hours at ambient temperature, quenched by addition of water and the mixture extracted with ethyl acetate (3x 50 ml). The combined organic extracts were washed with aqueous sodium hydrogen carbonate (saturated), dried over sodium sulfate and then concentrated in vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane / ethyl acetate 95:5) to afford 4-bromo-3-trifluoromethoxy-aniline (270 mg) and 2-bromo-5- trifluoromethoxy-aniline (1.45 g), which were both characterized by mass and NMR spectra. 4-bromo-3-trifluoromethoxy-aniline: MS (ES+) 256 / 258 (MH+); IH NMR (400 MHz, CDCl3) 3.5 (brs, 2H), 6.5 (d, IH), 6.7 (s, IH), 7.3 (d, IH). 2-bromo-5-trifluoromethoxy- aniline: MS (ES+) 256 / 258 (MH+); IH NMR (400 MHz, CDCl3) 4.2 (brs, 2H), 6.5 (d, IH), 6.6 (s, IH), 7.4 (d, IH).

Reference： [1]Patent: WO2011/3684,2011,A1 .Location in patent: Page/Page column 25

7
[ 887267-47-2 ]
[ 407-25-0 ]
[ 1262879-44-6 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In tetrahydrofuran; at 20℃; for 16h;	Reference Example 1-1N-(2-Bromo-5-trifluoromethoxyphenyl)-2,2,2-trifluoroacetamide Under ice-cooling, to a solution of <strong>[887267-47-2]2-bromo-5-trifluoromethoxyaniline</strong> (0.98 g) in tetrahydrofuran (10 mL) were added trifluoroacetic anhydride (0.79 mL) and pyridine (0.61 mL). The solution was stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure. To the residue was added ethyl acetate, and the organic layer was washed with 10% aqueous citric acid solution, a saturated aqueous sodium hydrogen carbonate solution, and saturated brine successively, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained crude product was purified by silica gel column chromatography (eluting solvent: hexane-ethyl acetate) to obtain the title compound (1.30 g).1H-NMR (CDCl3) delta ppm: 8.60-8.30 (2H, m), 7.65 (1H, d, J=8.9 Hz), 7.10-7.00 (1H, m)

Reference： [1]Patent: US2012/122931,2012,A1 .Location in patent: Page/Page column 16-17

8
[ 887267-47-2 ]
[ 1643795-99-6 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 7349 - 7353

9
[ 887267-47-2 ]
[ 1643796-14-8 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 7349 - 7353

10
[ 887267-47-2 ]
[ 501-53-1 ]
[ 1643796-29-5 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 7349 - 7353

11
[ 887267-47-2 ]
[ 98-80-6 ]
4-(trifluoromethoxy)biphenyl-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
198 mg	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃;Inert atmosphere;	Intermediate 117 4-(Trifluoromethoxy)biphenyl-2-amine 2-Bromo-5-(trifluoromethoxy)aniline (CAS 887267-47-2; 200 mg), phenylboronic acid (143 mg) and a 2 M aqueous solution of sodium carbonate (1.17 ml) were combined at r.t. under argon with dioxane (9.4 ml) and water (3.75 ml). [Iota, - Bis(diphenylphosphino)ferrocene]dichloropalladium(II), dichloromethane adduct (31.9 mg) was added to give yellow suspension. The reaction mixture was heated to 80 C and stirred overnight at 80 C. The reaction mixture was cooled down and filtered through glass fiber paper, washed with 30 mL water and 30 mL EtOAc, the layers were separated, the aqueous layer was back- extracted with EtOAc. The organic layers were combined, dried over MgS04 and concentrated in vacuo. The product was purified by flash chromatography (silical gel, 0% to 70% EtOAc in n- heptane) to give the title compound (198 mg) as a yellow oil.

Reference： [1]Patent: WO2014/146994,2014,A1 .Location in patent: Page/Page column 54-55

12
[ 32315-10-9 ]
[ 887267-47-2 ]
N-[5-(4-aminophenyl)pyridin-2-yl]-2,2-dimethylpropanamide [ No CAS ]
N-(5-{4-[([2-bromo-5-(trifluoromethoxy)phenyl]amino}carbonyl)amino]phenyl}pyridin-2-yl)-2,2-dimethylpropanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Triphosgene (0.09 g, 0.3 mmol) was dissolved in anhydrous CH2Cl2 (15 mL) and the mixture was stirred on the ice-bath for 15 min. 3-Bromo-5-(trifluoromethyl)aniline (0.16 g, 0.7 mmol) in anhydrous CH2Cl2 (10 mL) was added dropwise to the above mixture and stirring continued for 20 min. Et3N (0.12 mL, 0.89 mmol) diluted with CH2Cl2 (5 mL) was then added into the mixture. Stirring was continued for 20 min and a solution of Et3N (0.12 mL, 0.89 mmol), compound (9) (0.2 g, 0.74 mmol) in anhydrous CH2Cl2 (20 mL) was added. After completion of the action, the reaction was quenched with dilute Na2CO3. The organic layer was washed with water and brine, and dried over Na2SO4. After filtration and concentration in vacuo, the residues was purified by silica gel flash chromatography (PE/AcOEt = 3:1) yielding (W1).

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3228 - 3236

13
[ 82261-42-5 ]
[ 32315-10-9 ]
[ 887267-47-2 ]
N-[2-bromo-5-(trifluoromethoxy)phenyl]-N'-(4-pyridin-3-ylphenyl)urea [ No CAS ]