Butanoic acid, 2-bromo-, ethyl ester → Ethyl-alpha-(2,2,2-trifluoro-1-phenylethoxy)butyrate

HRID 1577589Notes

Reaction equation

HRID 1577589 reaction equation
[Na].[F:2][C:3]([F:13])([F:12])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[O-:5].[CH2:14]([O:16][C:17](=[O:22])[CH:18](Br)[CH2:19][CH3:20])[CH3:15]>CN(C)C=O>[CH2:14]([O:16][C:17](=[O:22])[CH:18]([O:5][CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([F:12])([F:13])[F:2])[CH2:19][CH3:20])[CH3:15]

Participants

4

Reactant 2

HCID 79039Butanoic acid, 2-bromo-, ethyl esterHCID 86738004Sodium 2,2,2-trifluoro-1-phenylethanolate

Product 1

HCID 20571125Ethyl-alpha-(2,2,2-trifluoro-1-phenylethoxy)butyrate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

10.3 g of the sodium-2,2,2-trifluoro-1-phenylethanolate, obtained according to the process of Step A, are transferred into a three-neck flask with 50 ml dimethylformamide. After complete mixing, there is slowly added while cooling with an ice-bath a cooled mixture of 9.4 g ethyl-2-bromobutyrate and 35 ml dimethylformamide. The reaction is strongly exothermic and external cooling is applied so that the temperature of the reaction mixture does not go over 20°. The stirring and the cooling of the mixture are kept for four days.

Workup

  1. additionAfter complete mixing, there is slowly added
  2. temperaturewhile cooling with an ice-bath
  3. temperatureexternal cooling
  4. customdoes not go over 20°
  5. temperatureThe stirring and the cooling of the mixture

Sources & evidence

ORD record
ord-89f43c426ef7414f959e713e505f8f4e
Source dataset
uspto-grants-1981_09
Patent number
US04288453

Reaction notes

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