3-(2-Bromo-5-(trifluoromethyl)phenyl)propanoic acid → 5-(Trifluoromethyl)indan-1-one

HRID 1191923Notes

Reaction equation

HRID 1191923 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[CH2:12][CH2:13][C:14]([OH:16])=O.C([Li])CCC>C1COCC1.CCCCCC>[F:11][C:8]([F:9])([F:10])[C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[C:14](=[O:16])[CH2:13][CH2:12]2

Participants

5

Reactant 2

HCID 248204723-(2-Bromo-5-(trifluoromethyl)phenyl)propanoic acidHCID 178418339Butyllithium

Product 1

HCID 121749875-(Trifluoromethyl)indan-1-oneYield 37.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent2×

Procedure

To a solution of 3-[2-bromo-5-(trifluoromethyl)phenyl]propanoic acid (2.8 g, 9.4 mmol) in THF (100 mL) and hexane (20 mL) at −78° C. was dropwise added a 2.5 M solution of n-butyllithium in hexane (8.3 mL). After the addition had been completed, the reaction was quenched with saturated NH4Cl. The resulting solution was extracted with ethyl acetate twice. The extracts were washed with saturated NaHCO3, brine, dried over MgSO4 and concentrated. The crude material was purified by flash chromatography on silica eluting with 10-20% EtOAc/hexane to afford the desired product as a white solid (0.7 g, 37%). LC/MS calculated for C10H7F3O: (M+H)+ 201. found 201.1.

Workup

  1. additionAfter the addition
  2. customthe reaction was quenched with saturated NH4Cl
  3. extractionThe resulting solution was extracted with ethyl acetate twice
  4. washThe extracts were washed with saturated NaHCO3, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe crude material was purified by flash chromatography on silica eluting with 10-20% EtOAc/hexane

Sources & evidence

ORD record
ord-15a5f144b016414b83bff2baf4a2f15b
Source dataset
uspto-grants-2014_03
Patent number
US08680104B2

Reaction notes

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