Hydrochloric Acid → 3-(4-Fluorophenyl)-6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-one

HRID 325864Notes

Reaction equation

HRID 325864 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH:12]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[CH2:13][C:14](O)=[O:15].C([Li])CCC.Cl>C(OCC)C>[F:23][C:20]1[CH:19]=[CH:18][C:17]([CH:12]2[C:3]3[C:4](=[CH:5][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:7][CH:2]=3)[C:14](=[O:15])[CH2:13]2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 131547143-[2-Bromo-4-(trifluoromethyl)phenyl]-3-(4-fluorophenyl)propanoic acidHCID 178418339Butyllithium

Product 1

HCID 30189253-(4-Fluorophenyl)-6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-oneYield 76.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 40 grams of 3-(2-bromo-4-trifluoromethylphenyl)-3-(4'-fluorophenyl)-propanoic acid in 750 milliliters of dry diethylether were added dropwise 90 milliliters of butyllithium (20% in hexane). The temperature was kept between -2 and -5 degrees Centigrade, and the addition time was about 10 minutes. The reaction mixture was stirred at zero degrees Centigrade for 11/2 hours; and then 400 milliliters of 2 N hydrochloric acid were added. The orgranic phase was separated and extracted twice with a 10% solution of sodium carbonate in water, then washed with water and dried over anhydrous potassium carbonate. After filtration and evaporation there was obtained 23 grams of crude 3-(4'-fluorophenyl)-6-trifluoromethyl-1-indanone. The oil was distilled in vacuo, and there was obtained 17 grams (57%) of pure 3-(4'-fluorophenyl)-6-trifluoromethyl-1-indanone boiling at 140 degrees Centigrade /0.2 mmHg.

Workup

  1. customwas kept between -2 and -5 degrees Centigrade
  2. customThe orgranic phase was separated
  3. extractionextracted twice with a 10% solution of sodium carbonate in water
  4. washwashed with water
  5. dry with materialdried over anhydrous potassium carbonate
  6. filtrationAfter filtration
  7. customevaporation there

Sources & evidence

ORD record
ord-0a423a433a4d4ae4a5fd08a7ac51ecb2
Source dataset
uspto-grants-1984_04
Patent number
US04443448

Reaction notes

Loading…