ChemicalBook CAS DataBase List 6-Chloroindole-3-carboxaldehyde

6-Chloroindole-3-carboxaldehyde synthesis

6synthesis methods

Product Name:6-Chloroindole-3-carboxaldehyde
CAS Number:703-82-2
Molecular formula:C9H6ClNO
Molecular Weight:179.6

17422-33-2

68-12-2

703-82-2

GENERAL STEPS: Oxalyl chloride (0.3 mL) was slowly added dropwise to ice-bath cooled N,N-dimethylformamide (DMF, 3 mL) under stirring conditions. The reaction mixture was stirred continuously at 0 °C for 1 hour. Subsequently, a solution of 6-chloroindole (4 mmol) dissolved in DMF (1.5 mL) was added slowly dropwise to the above reaction mixture. The resulting mixture was stirred and reacted at room temperature for 5 hours. Upon completion of the reaction, 2 N sodium hydroxide solution (2 mL) was added and the mixture was heated to 100°C maintained for 10 minutes. The reaction solution was cooled and extracted with ethyl acetate (3 x 50 mL). The organic phases were combined and washed sequentially with water and saturated saline. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by fast column chromatography with the eluent of ethyl acetate/petroleum ether (3:1, v/v) to give pure 6-chloroindole-3-carbaldehyde.

17422-33-2
335 suppliers
$10.00/1g

110-18-9 Synthesis

110-18-9
570 suppliers
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703-82-2
162 suppliers
$10.00/1g

Yield:703-82-2 72%

Reaction Conditions:

with water;iodine;oxygen;sodium carbonate in 1,4-dioxane at 100; under 760.051 Torr; for 36 h;Schlenk technique;Sealed tube;

Steps:

Experimental Procedures for the C3-Formylation of Indoles
General procedure: Under air, a 20 mL of Schlenk tube equipped with a stir bar was charged with indole 1 (0.2 mmol, 1 equiv),TMEDA (75 µL, 0.5 mmol, 2.5 equiv), Na₂CO₃(42.4 mg, 0.4mmol, 2.0 equiv), 1,4-dioxane (0.5 mL) and H₂O (100 µL). Then I₂ (101.5 mg, 0.4 mmol, 2.0 equiv) was added and the tube was sealed with a rubber plug and charged with O₂. The reaction mixture was stirred at 100 °C for 36 h in oil bath. After cooling to room temperature, the resultant mixture was evaporated with EtOAc (20 mL) under reduced pressure and the residue was purified by flash column chromatography on a silica gel to give the products.

References:

Zhang, Bo;Liu, Bin;Chen, Jianbin;Wang, Jiehui;Liu, Miaochang [Tetrahedron Letters,2014,vol. 55,# 41,p. 5618 - 5621] Location in patent:supporting information

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17422-33-2
335 suppliers
$10.00/1g

298-12-4 Synthesis