Acetic Acid → 5-bromo-2,3-dihydro-1H-indene-1-carboxylic acid

HRID 2046553Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2046553
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)C(=C1SCCCS1)[CH2:6][CH2:5]2.Cl.[C:18]([OH:21])(=[O:20])[CH3:19]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:19]([C:18]([OH:21])=[O:20])[CH2:6][CH2:5]2

Komponenten

4

Edukt 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 574194852-(5-Bromoindane-1-ylidene)-1,3-dithiane

Produkt 1

HCID 138400065-bromo-2,3-dihydro-1H-indene-1-carboxylic acidAusbeute 86 %

Versuchsvorschrift

To a mixture of 2-(5-bromo-indan-1-ylidene)-[1,3]dithiane (2.02 g, 6.45 mmol) in acetic acid (34 ml) was added 37% HCl (11 ml). After the addition, the brown mixture was heated to reflux for 3 h; then, the reaction mixture was allowed to cool to room temperature and was concentrated to dryness, using toluene as co-evaporating solvent to remove acetic acid and water. This process was repeated four times. The remaining brown oil was purified by chromatography (silica gel; CH2Cl2/EtOAc 100:0-0:100) to obtain the title compound as light brown solid (1.335 g, 86%). MS: 238.6 [M−H]−.

Aufarbeitung

  1. additionAfter the addition
  2. temperaturethe brown mixture was heated
  3. temperatureto reflux for 3 h
  4. concentrationwas concentrated to dryness
  5. customto remove acetic acid and water
  6. customThe remaining brown oil was purified by chromatography (silica gel; CH2Cl2/EtOAc 100:0-0:100)

Quellen und Nachweise

ORD-Eintrag
ord-6fcbc5a141334acbbea004827b88713b
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592426B2

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