Carbon Dioxide → Benzyl 4-bromobutanoate

HRID 2303337Notes

Reaction equation

HRID 2303337 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH2:8](OC(Cl)=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C.C(=O)=O>ClCCl.CN(C)C1C=CN=CC=1>[CH2:8]([O:6][C:5](=[O:7])[CH2:4][CH2:3][CH2:2][Br:1])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 758094-Bromobutyric acid

Product 1

HCID 3832489Benzyl 4-bromobutanoateYield 103.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To an ice cold solution of 5 g of 4-bromobutyric acid and 5.5 g of benzylchloroformate in 100 mL of dichloromethane was added 5 mL of triethylamine and then 700 mg of 4-dimethylaminopyridine. A vigorous exothermic reaction ensued with evolution of carbon dioxide. After stirring for 3 h, the mixture was diluted with 100 mL of dichloromethane and washed with 200 mL of saturated sodium bicarbonate, dried over magnesium sulfate, and concentrated to an oil. Azeotropic drying with toluene gave 8 g of 4-bromobutyric acid benzyl ester as a clear oil.

Workup

  1. customA vigorous exothermic reaction
  2. washwashed with 200 mL of saturated sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to an oil
  5. dry with materialAzeotropic drying with toluene

Sources & evidence

ORD record
ord-ba629f41050347cebb994873a88f7b22
Source dataset
uspto-grants-2002_08
Patent number
US06432976B1

Reaction notes

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