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

HRID 1733338
Notes
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Reaction equation

HRID 1733338 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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

Conditions

Temperature
0 °C

Procedure

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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° C. 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. extractionextracted with ether
  2. washThe organic layer is washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-412023af88c740949a2692fe25b2dfd1
Source dataset
uspto-grants-1980_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04241076

Reaction notes

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