Acetate → HCID 53862012, compound

HRID 1282864Notes

Reaction equation

HRID 1282864 reaction equation
[Br:1]Br.[C:3]([O-:6])(=[O:5])[CH3:4].[Cl:7][C:8]([Cl:19])([Cl:18])[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH2:11]>C(Cl)(Cl)(Cl)Cl.C([O-])(=O)C.[Ag+]>[C:3]([O:6][C:10]([CH2:11][Br:1])([CH2:9][C:8]([Cl:18])([Cl:19])[Cl:7])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:5])[CH3:4]

Participants

6

Reactant 3

HCID 175AcetateHCID 24408Bromine2×HCID 88346(3,3,3-Trichloro-1-methylenepropyl)benzene

Product 1

HCID 53862012HCID 53862012, compound

Reagents, catalysts & solvents 2

HCID 11246Silver acetateCatalystHCID 5943Carbon TetrachlorideSolvent3×

Procedure

Silver acetate (17.0 grams; 0.10 mole) was mixed with 200 ml. of carbon tetrachloride and the mixture cooled in an aqueous alcohol bath to about -11° to -13°C. A solution of bromine (16.0 grams; 0.10 mole) in 100 ml. of carbon tetrachloride was added dropwise to the acetate solution while maintaining the reaction mixture temperature below about -11°C. Upon the completion of the bromine addition, the reaction mixture was stirred at temperatures below about -11°C. for about 30 minutes. Following this period, a solution of α-(2,2,2-trichloroethyl)styrene (11.2 grams; 0.05 mole) in 100 ml of carbon tetrachloride was added dropwise to the reaction mixture over a period of about one hour, while maintaining the reaction mixture temperature below about 5°C. The reaction mixture was warmed to ambient temperatures and stirred for a period of from about 1 to about 15 hours. Following this period the reaction mixture was filtered and the recovered silver halide precipitate extracted with methylene chloride. The extract was combined with the filtrate and the mixture washed successively with 5% NaHSO3 (3-100 ml. portions) and 100 ml. of water and then dried over sodium sulfate. The organic product layer was then evaporated in vacuo to obtain the desired α-(bromomethyl)-α -(2,2,2-trichloroethyl)benzyl acetate as a light yellow oil.

Workup

  1. temperaturewhile maintaining the reaction mixture temperature below about -11°C
  2. waitFollowing this period
  3. temperaturewhile maintaining the reaction mixture temperature below about 5°C
  4. temperatureThe reaction mixture was warmed to ambient temperatures
  5. stirringstirred for a period of from about 1 to about 15 hours
  6. waitFollowing this period
  7. filtrationthe reaction mixture was filtered
  8. extractionthe recovered silver halide precipitate extracted with methylene chloride
  9. washthe mixture washed successively with 5% NaHSO3 (3-100 ml. portions) and 100 ml
  10. dry with materialof water and then dried over sodium sulfate
  11. customThe organic product layer was then evaporated in vacuo

Sources & evidence

ORD record
ord-cb8609352ac54db3baf684ae668a8c9f
Source dataset
uspto-grants-1976_08
Patent number
US03972913

Reaction notes

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