Ethyl Bromide → Ethyl (4-chlorophenyl)acetate

HRID 1710019Notes

Reaction equation

HRID 1710019 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.Br[CH2:13][CH3:14].N12CCCN=C1CCCCC2>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:13][CH3:14])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 15880(4-Chlorophenyl)acetic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 84177Ethyl (4-chlorophenyl)acetateYield 623.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 25 grams (0.147 mole) of 4-chlorophenylacetic acid in 250 ml of acetonitrile was stirred and 15.0 grams (0.0147 mole) of bromoethane, followed by 22.0 grams (0.147 mole) of 1,8-diazabicyclo[5.4.0]undec-7-ene, were added. Upon completion of addition the reaction mixture was cooled in a water bath while being stirred for 18 hours. The reaction mixture was concentrated under reduced pressure to one-half volume and then was added to 50 ml of water. The mixture was extracted with two portions of diethyl ether. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to yield 18.2 grams of ethyl (4-chlorophenyl)acetate.

Workup

  1. additionwere added
  2. additionUpon completion of addition the reaction mixture
  3. temperaturewas cooled in a water bath
  4. concentrationThe reaction mixture was concentrated under reduced pressure to one-half volume
  5. additionwas added to 50 ml of water
  6. extractionThe mixture was extracted with two portions of diethyl ether
  7. dry with materialThe combined extracts were dried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-58f9a797591647f1b75a04696784d7ce
Source dataset
uspto-grants-1990_08
Patent number
US04952580

Reaction notes

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