Benzyl Alcohol → Benzyl 2-bromo-2,2-difluoroacetate

HRID 1025252Notes

Reaction equation

HRID 1025252 reaction equation
C(O[K])(C)(C)C.[Br:7][C:8]([F:15])([F:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10].C(O)[C:17]1[CH:22]=[CH:21]C=[CH:19][CH:18]=1>CCCCCC>[Br:7][C:8]([F:15])([F:14])[C:9]([O:11][CH2:12][C:13]1[CH:21]=[CH:22][CH:17]=[CH:18][CH:19]=1)=[O:10]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 69585Ethyl bromodifluoroacetateHCID 178418922HCID 178418922, compound

Product 1

HCID 10378165Benzyl 2-bromo-2,2-difluoroacetateYield 58%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

1.60 g (14 mmol) of t-butoxypotassium was added to a solution prepared by dissolving 20.30 g (0.1 mol) of ethyl 2-bromo-2,2-difluoroacetate in 140 ml of benzyl alcohol and 1200 ml of hexane at 0° C. in a nitrogen atmosphere. The mixture was stirred at 0° C. for 1 hour. After confirming disappearance of the raw materials by thin-layer chromatography (TLC), the reaction was terminated by adding 120 ml of concentrated hydrochloric acid. The mixture was washed twice with water, washed twice with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After evaporating the solvent under reduced pressure, the product was purified by column chromatography to obtain 15.37 g of benzyl 2-bromo-2,2-difluoroacetate shown by the following formula (yield: 58%).

Workup

  1. customprepared
  2. customthe reaction was terminated
  3. additionby adding 120 ml of concentrated hydrochloric acid
  4. washThe mixture was washed twice with water
  5. washwashed twice with a saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter evaporating the solvent under reduced pressure
  8. customthe product was purified by column chromatography

Sources & evidence

ORD record
ord-9264c0c0b74e4c7eb3037507ccd5ffd2
Source dataset
uspto-grants-2014_05
Patent number
US08728706B2

Reaction notes

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