Triethylsilane → 4'-n-Pentyl-2,5-difluoro-4-bromobiphenyl

HRID 327361Notes

Reaction equation

HRID 327361 reaction equation
C([SiH](CC)CC)C.[C:8]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[C:24]([F:26])[C:23]([Br:27])=[CH:22][C:21]=2[F:28])=[CH:16][CH:15]=1)(=O)[CH2:9][CH2:10][CH2:11][CH3:12].C([O-])(O)=O.[Na+]>FC(F)(F)C(O)=O>[CH2:8]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[C:24]([F:26])[C:23]([Br:27])=[CH:22][C:21]=2[F:28])=[CH:16][CH:15]=1)[CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 147660524'-Pentanoyl-2,5-difluoro-4-bromobiphenyl

Product 1

HCID 147660534'-n-Pentyl-2,5-difluoro-4-bromobiphenyl

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Triethylsilane (7.0 g) is added dropwise over 2 h to a cooled, stirred (0° C.) solution of 1E (8.0 g) in trifluoroacetic acid (40 ml). The reaction mixture is stirred at room temperature overnight and poured into NaHCO3 solution. The product is extracted into ether twice and the combined ether layers are washed with water and dried (MgSO4). The solvent was removed in vacuo to yield an orange-brown oil. The crude product is distilled under reduced pressure (short path, 110°-120° C. at 0.01 mm Hg) to give a red oil.

Workup

  1. extractionThe product is extracted into ether twice
  2. washthe combined ether layers are washed with water
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed in vacuo
  5. customto yield an orange-brown oil
  6. distillationThe crude product is distilled under reduced pressure (short path, 110°-120° C. at 0.01 mm Hg)
  7. customto give a red oil

Sources & evidence

ORD record
ord-88e168a75b584d97b2f6ba639cfbe820
Source dataset
uspto-grants-1993_12
Patent number
US05273680

Reaction notes

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