Sulfuric Acid → Methyl 5-Fluoroindole-3-acetate

HRID 2381945Notes

Reaction equation

HRID 2381945 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C:12]([OH:14])=[O:13].S(=O)(=O)(O)O.[C:20]([O-])(O)=O.[Na+]>CO>[CH3:20][O:13][C:12](=[O:14])[CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=2)[NH:7][CH:6]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 967505-Fluoroindole-3-acetic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 21638377Methyl 5-Fluoroindole-3-acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (5-fluoro-1H-indol-3-yl)-acetic acid (1 g, 5.2 mmol) in MeOH (20 mL) is treated with sulfuric acid (20 μL) and stirred at rt for 1 h. This mixture is treated with 10% aqueous NaHCO3 (200 μL) and then concentrated in vacuo to afford (5-fluoro-1H-indol-3-yl)-acetic acid methyl ester, which is used in the next step without further purification. MS: 208 (M+H); 1H NMR (300 MHz, CD3OD): δ 3.68 (s, 3H), 3.72 (s, 2H), 6.86 (m, 1H), 7.16 (m, 1H), 7.21 (s, 1H), 7.28 (m, 1H).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2a4e6b82cd6e499086171da24fe1d1b0
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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