Bromine → Ethyl 8-bromo-12-acetoxyheptadecanoate

HRID 328762Notes

Reaction equation

HRID 328762 reaction equation
C([CH:4]([CH2:16][CH2:17][CH2:18][CH:19]([O:25][C:26](=[O:28])[CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])(O)=O.[Br:29]Br>C(Cl)(Cl)(Cl)Cl>[Br:29][CH:4]([CH2:16][CH2:17][CH2:18][CH:19]([O:25][C:26](=[O:28])[CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 2

HCID 24408BromineHCID 21317594HCID 21317594, compound

Product 1

HCID 21317595Ethyl 8-bromo-12-acetoxyheptadecanoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of ethyl 8-carboxy-12-acetoxyheptadecanoate (31.5 g., 0.079 mole), red mercuric oxide (12.8 g., 0.059 mole), and carbon tetrachloride (200 ml.) is stirred at room temperature while bromine (12.6 g., 0.079 mole) is added dropwise during one hour. The resulting mixture is heated at reflux for 1 hour. The mixture is then cooled, filtered, washed with dilute hydrochloric acid, water and brine and dried over sodium sulfate. The solution is evaporated in vacuo to leave the product as a yellow residual oil weighing 24.5 g. The product is purified by chromatography on a column containing 250 g. of silica gel using chloroform as eluting solvent. There is obtained 14.4 g. of purified ethyl 8-bromo-12-acetoxyheptadecanoate, a yellow oil with Rf 0.49 on silica gel thin layer chromatography with chloroform elution. pmr (CDCl3) δ 0.90 (3H,t); 2.03 (3H, s CH3CO); 4.07 (1H, m HCBr); 4.13 (2H, q); 4.92 (1H, m HCO).

Workup

  1. additionis added dropwise during one hour
  2. temperatureThe resulting mixture is heated
  3. temperatureat reflux for 1 hour
  4. temperatureThe mixture is then cooled
  5. filtrationfiltered
  6. washwashed with dilute hydrochloric acid, water and brine
  7. dry with materialdried over sodium sulfate
  8. customThe solution is evaporated in vacuo

Sources & evidence

ORD record
ord-87d15d81b3b04053b17505a342989008
Source dataset
uspto-grants-1977_04
Patent number
US04018802

Reaction notes

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