Hydrochloric Acid → 6-(Trifluoromethyl)-1-indanone

HRID 2387433Notes

Reaction equation

HRID 2387433 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[CH2:12][CH2:13][C:14]([OH:16])=O.C([Li])CCC.Cl>C1COCC1.CCCCCC>[F:11][C:8]([F:9])([F:10])[C:6]1[CH:7]=[C:2]2[C:3]([CH2:12][CH2:13][C:14]2=[O:16])=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 227541293-(2-Bromo-4-(trifluoromethyl)phenyl)propanoic acidHCID 178418339Butyllithium

Product 1

HCID 227541286-(Trifluoromethyl)-1-indanoneYield 51.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent2×

Procedure

To a solution of 3-[2-bromo-4-(trifluoromethyl)phenyl]propanoic acid (6.40 g, 21.5 mmol) in THF (300 mL) and hexane (80 mL) at −78° C. was added a 2.5 M solution of n-butyllithium in hexane (19 mL). After being stirred for 15 min, the mixture was poured into a 2 N HCl solution (150 mL). The two layers were separated and the water layer was extracted by ether. The combined organic layers were washed with NaHCO3 solution, water, brine, dried over MgSO4 and concentrated. Column chromatography on silica (10-20% EtOAC in hexane) provided the title compound (2.2 g, 51%) as an oil. MS calculated for C10H7F3O: (M+H)+ 201. found 201.0.

Workup

  1. customThe two layers were separated
  2. extractionthe water layer was extracted by ether
  3. washThe combined organic layers were washed with NaHCO3 solution, water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5b28675db9744deead07bd489bb6b11f
Source dataset
uspto-grants-2012_09
Patent number
US08268826B2

Reaction notes

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