Hydrochloric Acid → Methyl 5-bromo-2,3-dihydro-1H-indene-1-carboxylate

HRID 2046554Notes

Reaction equation

HRID 2046554 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([C:11]([OH:13])=[O:12])[CH2:6][CH2:5]2.Cl.[CH3:15]O>O1CCOCC1>[CH3:15][O:12][C:11]([CH:7]1[C:8]2[C:4](=[CH:3][C:2]([Br:1])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1)=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 138400065-bromo-2,3-dihydro-1H-indene-1-carboxylic acid

Product 1

HCID 13840001Methyl 5-bromo-2,3-dihydro-1H-indene-1-carboxylateYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (rac)-5-bromo-indan-1-carboxylic acid (1.326 g, 5.5 mmol) in MeOH (55 ml) was treated with 4N HCl in dioxane (15 ml) and the mixture was stirred at reflux for 7 h. The yellow solution was allowed to cool to room temperature and all volatiles were removed. The remaining brown oil was purified by chromatography (silica gel; heptane/EtOAc 95:5) to obtain the title compound as light yellow oil (1.31 g, 93%).

Workup

  1. temperatureat reflux for 7 h
  2. customall volatiles were removed
  3. customThe remaining brown oil was purified by chromatography (silica gel; heptane/EtOAc 95:5)

Sources & evidence

ORD record
ord-6c13f27d3db14acba4164c85fcc1f261
Source dataset
uspto-grants-2013_11
Patent number
US08592426B2

Reaction notes

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