Indole → Indole-3-Carboxaldehyde

Participants

Reaction Conditions

Reaction Steps

To a 500 mL round bottom flask containing 250 mL of DMF at 0° C. was added 105 mL (1.12 mol) of phosphorous oxychloride dropwise via an addition funnel. The reaction mixture was stirred for 30 min at 0° C. and then indole (0.51 mol) was added as a solid. The reaction mixture was heated to 80° C. for 6 h and then cooled in an ice bath. The cold solidified reaction was quenched with water (˜2 L) until all the solid had dissolved. The solution was kept cool and the pH was adjusted to ˜11 by the addition of 50% NaOH. The precipitate was filtered and washed with water. The filter cake was dried in vacuo in the presence of P2O5 to yield crude indole-3-carboxaldehyde (90-95% yield).

Provenance & Evidence