Bromine → 1-Acetyl-2-bromomethyl-3-methylindole-5-carboxylic acid ethyl ester

HRID 280617Notes

Reaction equation

HRID 280617 reaction equation
[Br:1]Br.[CH2:3]([O:5][C:6]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:17](=[O:19])[CH3:18])[C:12]([CH3:20])=[C:11]2[CH3:21])=[O:7])[CH3:4]>C(O)(=O)C>[CH2:3]([O:5][C:6]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:17](=[O:19])[CH3:18])[C:12]([CH2:20][Br:1])=[C:11]2[CH3:21])=[O:7])[CH3:4]

Participants

4

Reactant 2

HCID 24408BromineHCID 136630551-Acetyl-2,3-dimethylindole-5-carboxylic acid ethyl ester

Product 1

HCID 136630561-Acetyl-2-bromomethyl-3-methylindole-5-carboxylic acid ethyl esterYield 44.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (0.40 g) was added dropwise over 1 minute to a stirred solution of 1-acetyl-2,3-dimethylindole-5-carboxylic acid ethyl ester (0.65 g) in acetic acid (1.3 ml). After a few minutes a solid precipitated. The mixture was diluted with ca 5 ml. of ether and the solid was filtered off, washed with ether and dried to give 1-acetyl-2-bromomethyl-3-methylindole-5-carboxylic acid ethyl ester (0.38 g), m.p. 125°-130°. The product was unstable and was used directly in the next stage.

Workup

  1. customAfter a few minutes a solid precipitated
  2. additionThe mixture was diluted with ca 5 ml
  3. filtrationof ether and the solid was filtered off
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-0adac61fed794eb09d3d562c4dc01962
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

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