Trifluoroacetic acid → 5-Bromo-2-octylindan

HRID 1770165Notes

Reaction equation

HRID 1770165 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH:7]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:8]2=O)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>>[Br:1][C:2]1[CH:10]=[C:9]2[C:5](=[CH:4][CH:3]=1)[CH2:6][CH:7]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:8]2

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 200950616-Bromo-2-octyl-1-indanone

Product 1

HCID 235091535-Bromo-2-octylindanYield 93.1%

Procedure

Subsequently, 45.9 g (0.14M) of 6-bromo-2-n-octyl-1-indanone and 162.4 g (1.42M) of trifluoroacetic acid were placed in a 500 ml-reaction vessel. To the mixture, 41.4 g (3.57×10-1M) of triethylsilane was added dropwise in 15 minutes at room temperature. After the addition, the resultant mixture was heat-refluxed for 3.5 hours. After the reaction, the reaction mixture was poured into ice water and subjected to extraction with toluene, followed by successive washing with water and NaHCO3 aqueous solution, drying with anhydrous magnesium sulfate and distilling-off of the solvent. The resultant residue was subjected to vacuum distillation to obtain 40.3 g of 5-bromo-2-n-octylindan (Yield: 93.1%).

Workup

  1. additionAfter the addition
  2. customAfter the reaction
  3. extractionsubjected to extraction with toluene
  4. washby successive washing with water and NaHCO3 aqueous solution
  5. dry with materialdrying with anhydrous magnesium sulfate and distilling-off of the solvent
  6. distillationThe resultant residue was subjected to vacuum distillation

Sources & evidence

ORD record
ord-6b87104244234fcb8a5ccf3e7fd570ab
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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