Acetic Anhydride → Acetic acid 5-bromo-2-methyl-benzofuran-3-yl ester

HRID 216698Notes

Reaction equation

HRID 216698 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH:12]([C:14]([OH:16])=O)[CH3:13])=[C:6]([CH:10]=1)C(O)=O.[C:17](OC(=O)C)(=[O:19])[CH3:18].C([O-])(=O)C.[Na+]>>[Br:1][C:2]1[CH:10]=[CH:6][C:5]2[O:11][C:12]([CH3:13])=[C:14]([O:16][C:17](=[O:19])[CH3:18])[C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 591920275-Bromo-2-(1-carboxy-ethoxy)-benzoic acid

Product 1

HCID 59192036Acetic acid 5-bromo-2-methyl-benzofuran-3-yl esterYield 65%

Conditions

Temperature
150 °C

Procedure

A mixture of 5-bromo-2-(1-carboxy-ethoxy)-benzoic acid (31.2 g, 108 mmol), acetic anhydride (216 mL) and anhydrous sodium acetate (21.8 g, 266 mmol) is heated under reflux (150° C.) for 4 h. After cooling to room temperature the reaction mixture is carefully quenched with ice-cold water (500 mL). A white precipitate is formed which is collected by suction filtration, thoroughly washed with water and dried in vacuo at 45° C. to afford the title compound as a white powder (19.0 g, 70.6 mmol, 65%). MS (ES+): 269 (M(C11H979BrO3)+H)+.

Workup

  1. temperatureis heated
  2. temperatureAfter cooling to room temperature the reaction mixture
  3. customis carefully quenched with ice-cold water (500 mL)
  4. customA white precipitate is formed which
  5. filtrationis collected by suction filtration
  6. washthoroughly washed with water
  7. customdried in vacuo at 45° C.

Sources & evidence

ORD record
ord-cb4ca9c40d384ad292cf3b0ac49a6aa3
Source dataset
uspto-grants-2012_06
Patent number
US08193236B2

Reaction notes

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