Home Cart Sign in  
Chemical Structure| 408355-12-4 Chemical Structure| 408355-12-4

Structure of 408355-12-4

Chemical Structure| 408355-12-4

*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 [ 408355-12-4 ]

CAS No. :408355-12-4
Formula : C9H8BrNO
M.W : 226.07
SMILES Code : COC1=CC2=C(NC=C2)C(Br)=C1
MDL No. :MFCD04037873

Safety of [ 408355-12-4 ]

Application In Synthesis of [ 408355-12-4 ]

* 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 [ 408355-12-4 ]

[ 408355-12-4 ] Synthesis Path-Downstream   1~1

YieldReaction ConditionsOperation in experiment
59.8% (a) 5-Methoxy-7-bromoindole. 2-Bromo-4-methoxy-aniline (5.0 g, 24.7 mmol) was added dropwise to a solution of boron trichloride in methylene chloride (1.0 M, 27 mL, 27 mmol) cooled with ice water. The reaction mixture was warmed to room temperature, stirred for 30 min, and chloroacetonitrile (4.55 mL, 29.7 mmol) and aluminum chloride (4.54 g, 27.2 mmol) added, followed by 1,2-dichloroethane (32 mL). The reaction mixture was heated to 70 C. to distill off methylene chloride, and then refluxed for 24 h. The mixture was cooled to 0-5 C., treated with 2.5 M HCl (44 mL) at 0~5 C. carefully, and then heated to 80 C. for 1 h until all solids dissolved. The aqueous layer was separated and extracted with methylene chloride. The combined organic layers were washed with water and brine, dried (sodium sulfate) and concentrated a yellow solid, that was used without further purification. The crude product was taken into dioxane (19 mL) and water (2.1 mL), and treated with sodium borohydride (0.46 g, 12.2 mmol) in portions. After 30 min at room temperature, all the starting material had been consumed, and the reaction mixture was heated to reflux overnight. The mixture was then cooled to room temperature, treated with 0.1 N hydrochloric acid (195 mL), diluted with ethyl acetate, treated with concentrated hydrochloric acid and trifluoroacetic acid and stirred until all the hydroxy-intermediate was converted to the final product. The reaction mixture was then extracted with ethyl acetate, and the extract was washed with sodium bicarbonate, water and brine, dried (Na2SO4) and concentrated. Column chromatography on silica gel (hexanes/ethyl acetate) gave 4-methoxy-7-bromoindole (1.5 g, 59.8%). 1H NMR (400 MHz, CDCl3) 3.77 (s, 3H), 6.47~6.49 (m, 1H), 6.99 (s, 2H), 7.17(m, 1H), 8.11 (br, 1H); MS (ES, m/z): C9H8BrNO: 228 (M+(79Br)+1), 226.01 (M+(81Br)+1), 224.03 (M+(79Br)-1), 226.04 (M+(81Br)-1).
 

Historical Records