Trifluoroacetic acid → 4-Octyl-2'-fluoro-4'-bromobiphenyl

HRID 326962Notes

Reaction equation

HRID 326962 reaction equation
[C:1]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=2[F:23])=[CH:12][CH:11]=1)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>O>[CH2:1]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=2[F:23])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 189854264-Octanoyl-2'-fluoro-4'-bromobiphenyl

Product 1

HCID 147662924-Octyl-2'-fluoro-4'-bromobiphenylYield 71.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a reactor were placed 3.75 g of 4-octanoyl-2'-fluoro-4'-bromobiphenyl and 20 ml of trifluroacetic acid, to which was added 2.4 g of triethylsilane at room temperature and stirred for 6 hours. Then, the reaction solution was added into water, extracted into benzene, washed sequentially with water, aqueous sodium hydrogencarbonate, and again water, and dehydrated over Glauber's salt. After the solvent was distilled off, the residue was evaporated in a glass tube oven (GTO) to obtain 2.56 g of 4-octyl-2'-fluoro-4'-bromobiphenyl (71.1%).

Workup

  1. customIn a reactor were placed
  2. extractionextracted into benzene
  3. washwashed sequentially with water, aqueous sodium hydrogencarbonate, and again water
  4. distillationAfter the solvent was distilled off
  5. customthe residue was evaporated in a glass tube oven (GTO)

Sources & evidence

ORD record
ord-2217cc47ec4d4b8f847a904bcca84492
Source dataset
uspto-grants-1993_12
Patent number
US05271867

Reaction notes

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