ChemicalBook CAS DataBase List 5-BROMO-2-METHYLINDOLE

5-BROMO-2-METHYLINDOLE synthesis

9synthesis methods

Product Name:5-BROMO-2-METHYLINDOLE
CAS Number:1075-34-9
Molecular formula:C9H8BrN
Molecular Weight:210.07

5-BroMo-2-Methylindole can be used as organic synthesis intermediate and pharmaceutical intermediate, mainly in laboratory research and development process. It was prepared from o-nitro benzaldehydes, phosphorane, triphenyl phosphine and diphenyl ether heated at 260 ℃ for 1 h.

95-20-5 Synthesis

95-20-5
384 suppliers
$5.00/10g

1075-34-9
146 suppliers
$8.00/100mg

Yield: 75%

Reaction Conditions:

Stage #1:2-methyl-1H-indole with sulfuric acid;silver sulfate for 0.5 h;Cooling with ice;
Stage #2: with bromine at 20; for 4.5 h;

Steps:

75.1
Step 1. 5-Bromo-2-methyl-7H-indoleTo a solution of 2-methyl-iH-indole (5.0 g, 38.12 mmol) in sulfuric acid (80 mL) was added Ag₂S0₄ (12.5 g, 40.06 mmol) with ice cooling, and the solution was stirred for 30 min. Then Br₂ (6.4 g, 40.05 mmol) was added to the solution dropwise over 30 min. After the solution was stirred for 4 h at room temperature, the reaction was then quenched by the addition of water/ice (300 mL). The reaction mixture was extracted with dichloromethane (3 x 200 mL) and the organic layers combined, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 5-bromo-2-methyl-7H-indole as a light brown solid (6 g, 75%).LC/MS (ES, m/z): [M+H]⁺ 211.0'H-NMR (300 MHz, CDC1₃): δ 11.23 (s, 1Η), 7.56 (s, 1Η), 7.21 (d, / = 8.7 Hz, 1H), 7.07 - 7.09 (m, 1H), 6.11 (s, 1H), 2.38 (s, 3H)

References:

BIOENERGENIX;MCCALL, John M.;ROMERO, Donna L.;KELLY, Robert C. WO2012/119046, 2012, A2 Location in patent:Page/Page column 161

20357-20-4 Synthesis