Methanol → methyl(5-bromo-1H-inden-2-yl)acetate

HRID 860868Notes

Reaction equation

HRID 860868 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH:7]([CH2:12][C:13]([OH:15])=[O:14])[CH:8]2O)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:21]O>>[Br:1][C:2]1[CH:10]=[C:9]2[C:5](=[CH:4][CH:3]=1)[CH2:6][C:7]([CH2:12][C:13]([O:15][CH3:21])=[O:14])=[CH:8]2

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric Acid2×HCID 67104698(6-bromo-1-hydroxy-2,3-dihydro-1H-inden-2-yl)acetic Acid

Product 1

HCID 85969236methyl(5-bromo-1H-inden-2-yl)acetate

Conditions

Temperature
10 °C

Procedure

The product from Example 52B (1.35 g, 5 mmol) in methanol (12 mL) was treated with concentrated sulfuric acid (2 mL) and heated to gentle reflux. After 2 hours, additional sulfuric acid was added (1 mL) and heating was continued for another 2 hours. The mixture was concentrated under vacuum and the residue was diluted with water (15 mL). The mixture was cooled to 10° C., filtered, and the filter cake washed with water (5 mL) and dried to provide the title compound. 1H NMR (CDCl3) δ 3.42 (s, 2H); 3.55 (s, 2H); 3.74 (s, 3H); 6.65 (m, 1H); 7.22-7.31 (m, 2H), 7.44 (m, 1H).

Workup

  1. temperatureheated to gentle reflux
  2. temperatureheating
  3. waitwas continued for another 2 hours
  4. concentrationThe mixture was concentrated under vacuum
  5. additionthe residue was diluted with water (15 mL)
  6. filtrationfiltered
  7. washthe filter cake washed with water (5 mL)
  8. customdried

Sources & evidence

ORD record
ord-9a51db15110d4ccfb2bd4098d72c4ab1
Source dataset
uspto-grants-2006_12
Patent number
US07153889B2

Reaction notes

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