Water → Ethyl 3-Bromoindole-2-carboxylate

HRID 967107Notes

Reaction equation

HRID 967107 reaction equation
[Br:1]Br.[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]1[C:12]([O:14][CH2:15][CH3:16])=[O:13].O>CN(C=O)C>[Br:1][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[NH:3][C:4]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 73125Ethyl indole-2-carboxylate

Product 1

HCID 4715017Ethyl 3-Bromoindole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of bromine (2.72 ml) in DMF was added dropwise over 10 mins to a solution of ethyl indole-2-carboxylate in DMF. The reaction was stirred for 30 mins, then poured into water to precipitate a pale yellow solid which was filtered off and recrystallized from ethyl acetate to give the desired starting material as white needles (10.2 g, 72%), mp 150-151°; NMR δ (CDCl3) 1.44 (t, 3H), 4.45 (q, 2H), 7.22 (m, 11H), 7.38 (m, 2H), 7.66 (d, 1H), 9.27 (bs, 1H); M/z (−) 268 (M+), 266, 196, 194.

Workup

  1. customto precipitate a pale yellow solid which
  2. filtrationwas filtered off
  3. customrecrystallized from ethyl acetate
  4. customto give the

Sources & evidence

ORD record
ord-e39a02448b7a473bb2cc789b69be8b72
Source dataset
uspto-grants-2005_10
Patent number
US06953809B2

Reaction notes

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