Water → 5-Bromo-1-methyl-2,3-dihydro-1H-indene-1-carboxylic acid

HRID 2046556Notes

Reaction equation

HRID 2046556 reaction equation
C[O:2][C:3]([C:5]1([CH3:15])[C:13]2[C:8](=[CH:9][C:10]([Br:14])=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].C[Si](C)(C)[O-].[K+].O>C1COCC1>[Br:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[C:5]([CH3:15])([C:3]([OH:4])=[O:2])[CH2:6][CH2:7]2

Participants

5

Reactant 3

HCID 962WaterHCID 23668039Potassium trimethylsilanolateHCID 57419486Methyl 5-bromo-1-methyl-2,3-dihydro-1H-indene-1-carboxylate

Product 1

HCID 574194875-Bromo-1-methyl-2,3-dihydro-1H-indene-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (rac)-5-bromo-1-methyl-indan-1-carboxylic acid methyl ester (1.318 g, 4.9 mmol) and potassium trimethylsilanolate (3.14 g, 24.5 mmol) in dry THF (25 ml) was stirred at reflux for 1 h. The reaction mixture was allowed to cool to room temperature, water was added and the mixture was extracted two times with tert-butyl methylether. The pH of the aqueous layer was carefully adjusted to 3 by addition of 1N HCl and the aqueous layer was extracted two times with EtOAc. The combined EtOAc-layers were washed with brine, dried with Na2SO4 and evaporated. Toluene was added to the remaining residue and it was evaporated to remove water. The title compound was obtained as light yellow solid (1.204 g, 96%). MS: 252.7 [M−H]−.

Workup

  1. temperatureat reflux for 1 h
  2. extractionthe mixture was extracted two times with tert-butyl methylether
  3. additionThe pH of the aqueous layer was carefully adjusted to 3 by addition of 1N HCl
  4. extractionthe aqueous layer was extracted two times with EtOAc
  5. washThe combined EtOAc-layers were washed with brine
  6. dry with materialdried with Na2SO4
  7. customevaporated
  8. additionToluene was added to the remaining residue and it
  9. customwas evaporated
  10. customto remove water

Sources & evidence

ORD record
ord-fa231b32fed4492b813a3c30b2d82e22
Source dataset
uspto-grants-2013_11
Patent number
US08592426B2

Reaction notes

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