Trifluoroacetic acid → 5-(2-bromoethyl)-2,3-dihydro-1H-indene

HRID 2267205Notes

Reaction equation

HRID 2267205 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[Br:10][CH2:11][C:12](Br)=O.[Al+3].[Cl-].[Cl-].[Cl-].FC(F)(F)C(O)=O>C(Cl)Cl.C([SiH](CC)CC)C>[Br:10][CH2:11][CH2:12][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[CH2:1][CH2:2][CH2:3]2

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10326IndaneHCID 61147Bromoacetyl bromideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 212240805-(2-bromoethyl)-2,3-dihydro-1H-indene

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 12052TriethylsilaneSolvent

Procedure

2 ml (0.016 mol) of indan in 33 ml of methylene chloride and 1.6 ml (0.019 mol) of bromoacetyl bromide are mixed at 0° C. 2.27 g (0.017 mol) of AlCl3 are slowly added and the medium is allowed to return to room temperature and stirred for 2 hours. The mixture is poured into water/ice and extracted with methylene chloride. The organic phase is dried, filtered and the solvent is evaporated off under reduced pressure. The crude reaction product is crystallized from hexane. A white solid is separated (m.p. 57.8-58.1° C.) corresponding to the acylation product. 1.67 g (7 mmol) of this product are dissolved in 3.9 ml of triethylsilane and 3.9 ml of trifluoroacetic acid and the medium is heated at 80° C. for two hours. The medium is poured into an ice/NaOH mixture and extracted with ethyl acetate. The title compound is obtained.

Workup

  1. customto return to room temperature
  2. extractionextracted with methylene chloride
  3. customThe organic phase is dried
  4. filtrationfiltered
  5. customthe solvent is evaporated off under reduced pressure
  6. customThe crude reaction product
  7. customis crystallized from hexane
  8. customA white solid is separated (m.p. 57.8-58.1° C.) corresponding to the acylation product
  9. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-d8739537a70b42ea8bb8baf366a65459
Source dataset
uspto-grants-2010_12
Patent number
US07858824B2

Reaction notes

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