Home Cart Sign in  
Chemical Structure| 865886-83-5 Chemical Structure| 865886-83-5

Structure of 865886-83-5

Chemical Structure| 865886-83-5

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 865886-83-5 ]

CAS No. :865886-83-5
Formula : C7H4BrF2NO3
M.W : 268.01
SMILES Code : FC(F)OC1=CC=C([N+]([O-])=O)C(Br)=C1
MDL No. :MFCD18390949

Safety of [ 865886-83-5 ]

Application In Synthesis of [ 865886-83-5 ]

* 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 [ 865886-83-5 ]

[ 865886-83-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 383-62-0 ]
  • [ 5470-65-5 ]
  • [ 865886-83-5 ]
YieldReaction ConditionsOperation in experiment
75% With sodium hydroxide; In DMF (N,N-dimethyl-formamide); at 0 - 70℃; for 16.25h; 3-Bromo-4-nitrophenol (10.0 mmol) was added to a suspension of sodium hydroxide (29.0 mmol) in N, N-dimethylformamide (15 mL) and the suspension was maintained for 15 min at rt. The reaction mixture was cooled to 0 °C and was treated with <strong>[383-62-0]ethyl chlorodifluoroacetate</strong> (20.0 mmol). The reaction mixture was heated at 70 °C for 16 h and was concentrated. The residue was diluted with ice water (200 mL) and was extracted with ethyl acetate (3x100 mL). The combined organic layers were dried (magnesium sulfate) and concentrated to provide the difluoromethyl ether in 75percent yield as a yellow oil.
75% With sodium hydroxide; In N,N-dimethyl-formamide; at 0 - 70℃; for 16.25h; 3-Bromo-4-nitrophenol (10.0 mmol) was added to a suspension of sodium hydroxide (29.0 mmol) in N,N-dimethylformamide (15 mL) and the suspension was maintained for 15 min at rt. The reaction mixture was cooled to 0° C. and was treated with <strong>[383-62-0]ethyl chlorodifluoroacetate</strong> (20.0 mmol). The reaction mixture was heated at 70° C. for 16 h and was concentrated. The residue was diluted with ice water (200 mL) and was extracted with ethyl acetate (3.x.100 mL). The combined organic layers were dried (magnesium sulfate) and concentrated to provide the difluoromethyl ether in 75percent yield as a yellow oil.
75% Procedure 5 Procedure 5 provides a method for the preparation of 5-difluoromethoxyindazole-3-acid from 3-bromo-4-nitrophenol. 3-Bromo-4-nitrophenol (10.0 mmol) was added to a suspension of sodium hydroxide (29.0 mmol) in N,N-dimethylformamide (15 mL) and the suspension was maintained for 15 min at rt. The reaction mixture was cooled to 0° C. and was treated with <strong>[383-62-0]ethyl chlorodifluoroacetate</strong> (20.0 mmol). The reaction mixture was heated at 70° C. for 16 h and was concentrated. The residue was diluted with ice water (200 mL) and was extracted with ethyl acetate (3*100 mL). The combined organic layers were dried (magnesium sulfate) and concentrated to provide the difluoromethyl ether in 75percent yield as a yellow oil.
  • 2
  • [ 383-62-0 ]
  • [ 865886-83-5 ]
YieldReaction ConditionsOperation in experiment
75% 3-Bromo-4-nitrophenol (10.0 mmol) was added to a suspension of sodium hydroxide (29.0 mmol) in N, N-dimethylformamide (15 mL) and the suspension was maintained for 15 min at rt. The reaction mixture was cooled to 0 C and was treated with <strong>[383-62-0]ethyl chlorodifluoroacetate</strong> (20.0 mmol). The reaction mixture was heated at 70 C for 16 h and was concentrated. The residue was diluted with ice water (200 mL) and was extracted with ethyl acetate (3x100 mL). The combined organic layers were dried (magnesium sulfate) and concentrated to provide the difluoromethyl ether in 75% yield as a yellow oil. Diethyl malonate (328 mmol) was added dropwise to a suspension of sodium hydride (328 mmol) in dimethylsulfoxide (40 mL) at 0 C. The reaction mixture was warmed to 60 C and maintained for 0.5 h. A solution of the difluoromethyl ether (149 mmol) in dimethylsulfoxide (80 mL) was added dropwise and the reaction mixture was heated at 100 C for 5 h. The cooled solution was poured onto ice water, and the aqueous layer was extracted with dichloromethane (3x100 mL). The combined organic layers were dried (magnesium sulfate) and concentrated to give the crude diester in 112% yield as an oil. The diester (167 mmol), sodium hydroxide (500 mmol), and water (335 mL) were combined and heated at 60 C for 1 h. The reaction mixture was allowed to cool to rt and the aqueous layer was washed with dichloromethane (3x100 mL). The pH of the aqueous layer was cautiously adjusted to 1 with concentrated hydrochloric acid and the reaction mixture was heated at 60 C for 1 h. The suspension was cooled to 5 C and the solids were collected by filtration and dried to provide the acid in 61 % yield. Acetyl chloride (203 mmol) was added dropwise to ethanol (300 mL) at 0 C. After 0.5 h, the acid (101 mmol) was added and the reaction mixture was heated at reflux for 15 h. The reaction mixture was concentrated and the residue was partitioned between dichloromethane (200 mL) and saturated sodium bicarbonate (100 mL). The aqueous layer was further extracted with dichloromethane (2x200 mL) and the combined organic layers were dried (magnesium sulfate) and concentrated to provide the ester in 60% yield as a brown oil. The ester (60.4 mmol) was dissolved in ethanol (103 mL), diluted with water (71 mL), and was treated with ammonium chloride (243 mmol) and iron powder (301 mmol). The reaction mixture was heated at reflux for 10 minutes and the suspension was filtrated through Celite and the filter cake was washed with ethanol three times. The filtrate was concentrated, the residue was suspended in 2 N hydrochloric acid and was stirred vigorously for 0.5 h. The aqueous layer was washed with ethyl acetate (3x50mL) and the pH adjusted to 9-10 with 5 M sodium hydroxide. The aqueous layer was extracted with chloroform (3xlOOmL) and the combined organic layers were dried (magnesium sulfate). Acetic anhydride (392 mmol), isoamyl nitrite (291 mmol), and potassium acetate (51.0 mmol) were added to the organic layer and the suspension was heated at reflux for 16 h. The solution was evaporated and the residue was partitioned between saturated sodium bicarbonate (50 mL) and dichloromethane (100 mL). The aqueous layer was further extracted with dichloromethane (2x100 mL) and the combined organic layers were dried (magnesium sulfate) and concentrated to provide the N-acetylindazole ester in 79% yield as a brown oil. The ester (63.8 mmol), sodium hydroxide (193 mmol), and water (65 mL) were combined and the reaction was maintained for 24 h at 60 C. After cooling to rt, the aqueous layer was washed with dichloromethane (3x50mL). The aqueous layer was adjusted to pH 1 with concentrated hydrochloric acid. The precipitated solids were collected by filtration, washed with water and dichloromethane, and dried to provide the acid in 27% yield. The acid was coupled with 1,4-diazabicyclo[3.2.2]nonane according to procedure A.
75% 3-Bromo-4-nitrophenol (10.0 mmol) was added to a suspension of sodium hydroxide (29.0 mmol) in N,N-dimethylformamide (15 mL) and the suspension was maintained for 15 min at rt. The reaction mixture was cooled to 0 0C and was treated with <strong>[383-62-0]ethyl chlorodifluoroacetate</strong> (20.0 mmol). The reaction mixture was heated at 70 0C for 16 h and was concentrated. The residue was diluted with ice water (200 mL) and was extracted with ethyl acetate (3x100 mL). The combined organic layers were dried (magnesium sulfate) and concentrated to provide the difluoromethyl ether in 75% yield as a yellow oil.
 

Historical Records

Technical Information

Categories