Triethylsilane → 4-Bromo-2-fluoro-4'-propyl-1,1'-biphenyl

HRID 1755615Notes

Reaction equation

HRID 1755615 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15](=O)[CH2:16][CH3:17])=[CH:11][CH:10]=1.C([SiH](CC)CC)C.C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 8220021-(4'-Bromo-2'-fluorobiphenyl-4-yl)propan-1-one

Product 1

HCID 227175064-Bromo-2-fluoro-4'-propyl-1,1'-biphenylYield 84.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Procedure

29 g of 2-fluoro-4-bromo-4'-propionylbiphenyl was dissolved in 72 ml of trifluoroacetic acid and stirred. 24 g of triethylsilane was dropwise added thereto at room temperature over a period of 30 minutes. After this was stirred for 2 hours, 900 ml of an aqueous saturated sodium hydrogencarbonate solution was dropwise added thereto so that the excess trifluoroacetic acid was decomposed. This was extracted with chloroform and then washed three times with water, and chloroform was removed by distillation. The residue was distilled under reduced pressure (b.p. 140° to 145° C./2 mmHg) to obtain 23.4 g of 2-fluoro-4-bromo-4'-propylbiphenyl.

Workup

  1. stirringAfter this was stirred for 2 hours
  2. extractionThis was extracted with chloroform
  3. washwashed three times with water, and chloroform
  4. customwas removed by distillation
  5. distillationThe residue was distilled under reduced pressure (b.p. 140° to 145° C./2 mmHg)

Sources & evidence

ORD record
ord-3354ee80d5dd44989ab7c0622cfa8bf5
Source dataset
uspto-grants-1995_08
Patent number
US05437815

Reaction notes

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