1-(3,5-Bis(trifluoromethyl)phenyl)ethanol → 1-(1-Bromoethyl)-3,5-bis(trifluoromethyl)benzene

HRID 1289951Notes

Reaction equation

HRID 1289951 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:13](O)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[Br-:18].[Br-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:13]([Br:18])[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

4

Reactant 2

HCID 64257391-(3,5-Bis(trifluoromethyl)phenyl)ethanolHCID 12890784Triphenylphosphane dibromide

Product 1

HCID 129473971-(1-Bromoethyl)-3,5-bis(trifluoromethyl)benzeneYield 74.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1.89 g of (+/-)-1-(3,5-bis(trifluoromethy)-phenyl)-1-hydroxyethane prepared as in Example 5, Step A in 50 mL of acetonitrile at room temperature was added 5.15 g of triphenylphosphine dibromide. After 1.5 h, the reaction was partitioned between ether and water and the ether layer was washed with brine, dried with sodium sulfate and evaporated. The product was triturated with hexanes, filtered to remove the solid and reconcentrated. The residue was purified by flash chromatography using hexanes to provide 1.75 g of title compound as an oil.

Workup

  1. customthe reaction was partitioned between ether and water
  2. washthe ether layer was washed with brine
  3. dry with materialdried with sodium sulfate
  4. customevaporated
  5. customThe product was triturated with hexanes
  6. filtrationfiltered
  7. customto remove the solid
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-d8dbe93b7c704cfbb4a54f30704769b1
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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