1-Bromo-1,2,2-trifluoroethene → Methyl 3-(2'-bromo-1',1',2'-trifluoroethoxy)-benzoate

HRID 1762407Notes

Reaction equation

HRID 1762407 reaction equation
[Br:1][C:2]([F:6])=[C:3]([F:5])[F:4].[OH:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12].[OH-].[K+]>CC(C)=O>[Br:1][CH:2]([F:6])[C:3]([F:5])([F:4])[O:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 117301-Bromo-1,2,2-trifluoroetheneHCID 14797Potassium HydroxideHCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 14461297Methyl 3-(2'-bromo-1',1',2'-trifluoroethoxy)-benzoateYield 68%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

72.3 parts by weight of bromotrifluoroethene are passed, over 10 hours, into a mixture of 45.6 parts by weight of methyl 3-hydroxybenzoate and 9.5 parts by weight of potassium hydroxide powder in 50 parts by weight of acetone under reflux at 45°-52° C. After having been concentrated on a rotary evaporator under reduced pressure, the reaction mixture is taken up in methylene chloride and this solution is extracted with sodium bicarbonate solution, dried and concentrated. Methyl 3-(2'-bromo-1',1',2'-trifluoroethoxy)-benzoate of nD 25 =1.4850 is obtained in a yield of 68% of theory, and can be hydrolyzed, in a yield of 98% of theory, to 3-(2'-bromo-1',1',2'-trifluoroethoxy)-benzoic acid, of melting point 88°-90° C..

Workup

  1. temperatureunder reflux at 45°-52° C
  2. concentrationAfter having been concentrated on a rotary evaporator under reduced pressure
  3. extractionthis solution is extracted with sodium bicarbonate solution
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1bf31d9e472544d0898bced939387ad7
Source dataset
uspto-grants-1989_05
Patent number
US04832879

Reaction notes

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