Allyl bromide → 1,1,1-trifluoro-4-penten-2-ol

HRID 643886Notes

Reaction equation

HRID 643886 reaction equation
[In].[CH2:2](Br)[CH:3]=[CH2:4].C(O[CH:9]([OH:14])[C:10]([F:13])([F:12])[F:11])C>O>[F:13][C:10]([F:11])([F:12])[CH:9]([OH:14])[CH2:4][CH:3]=[CH2:2]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 9897Ethanol, 1-ethoxy-2,2,2-trifluoro-HCID 5359967Indium

Product 1

HCID 109096421,1,1-trifluoro-4-penten-2-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of indium powder (2.3 g, 20 mmol) in water is added allyl bromide (2.5 mL, 30 mmol) followed by trifluoroacetaldehyde ethyl hemiacetal (1.3 mL, 10 mmol). The reaction mixture is stirred for 16 h and then extracted with t-butyl methyl ether (50 mL). The organic layer is washed with water, brine, dried with Na2SO4 and concentrated to give the title compound as a colorless oil.

Workup

  1. extractionextracted with t-butyl methyl ether (50 mL)
  2. washThe organic layer is washed with water, brine
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-636cfc354b1d4693a020b3939d191a51
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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