Trifluoroalanine → 2-Bromo-3,3,3-trifluoropropanoic acid

HRID 262708Notes

Reaction equation

HRID 262708 reaction equation
[F:1][C:2]([F:9])([F:8])[C@@H:3]([C:5]([OH:7])=[O:6])N.N([O-])=O.[Na+].[Br-:14].[K+]>S(=O)(=O)(O)O>[Br:14][CH:3]([C:2]([F:9])([F:8])[F:1])[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 87122TrifluoroalanineHCID 253877Potassium BromideHCID 23668193Sodium Nitrite

Product 1

HCID 136803062-Bromo-3,3,3-trifluoropropanoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

3,3,3-Trifluoroalanine (88 g.) is dissolved in a mixture of potassium bromide (250 g.) and 2.5 N sulfuric acid (1.240 ml.). The solution is chilled to 0° with an ice-salt bath and sodium nitrite (65.5 g.) is added in small portions over a one hour period with vigorous stirring. The reaction mixture is stirred in the cooling bath for another hour and then extracted with ether. The organic layer is washed with water, dried over magnesium sulfate and concentrated to dryness in vacuo to yield 2-bromo-3,3,3-trifluoropropanoic acid.

Workup

  1. temperatureThe solution is chilled to 0° with an ice-salt bath
  2. extractionextracted with ether
  3. washThe organic layer is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-a2c58975a8c041c69d9ea80352ea96ec
Source dataset
uspto-grants-1979_05
Patent number
US04154935

Reaction notes

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