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

HRID 1769565Notes

Reaction equation

HRID 1769565 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

A reaction vessel was charged with 3.75 g of 4-octanoyl-2'-fluoro-4'-bromobiphenyl and 20 ml of trifluoroacetic acid. To the mixture was added dropwise 2.4 g of triethylsilane with stirring at room temperature. After stirring for 6 hours, the reaction liquid was poured into water and the mixture was extracted with benzene. The benzene extract was washed successively with water, an aqueous solution of sodium hydrogen carbonate and water, and then dried over Glauber's salt. The solvents were distilled off and the residue was distilled in a glass tube oven (GTO) to obtain 2.56 g (71.1%) of 4-octyl-2'-fluoro-4'-bromobiphenyl. GTO-set temperature: 150° C./0.2 mmHg.

Workup

  1. stirringAfter stirring for 6 hours
  2. customthe reaction liquid
  3. extractionthe mixture was extracted with benzene
  4. extractionThe benzene extract
  5. washwas washed successively with water
  6. dry with materialan aqueous solution of sodium hydrogen carbonate and water, and then dried over Glauber's salt
  7. distillationThe solvents were distilled off
  8. distillationthe residue was distilled in a glass tube oven (GTO)

Sources & evidence

ORD record
ord-2782fb43374f41399aaaf810bc2ad426
Source dataset
uspto-grants-1995_01
Patent number
US05382380

Reaction notes

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