Bromine → Ethyl 8-acetyl-12-(acetyloxy)-8-bromoheptadecanoate

HRID 1439488Notes

Reaction equation

HRID 1439488 reaction equation
[Br:1]Br.[C:3]([CH:6]([CH2:18][CH2:19][CH2:20][CH:21]([O:27][C:28](=[O:30])[CH3:29])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])(=[O:5])[CH3:4]>C(Cl)(Cl)(Cl)Cl>[C:3]([C:6]([Br:1])([CH2:18][CH2:19][CH2:20][CH:21]([O:27][C:28](=[O:30])[CH3:29])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])(=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 24408BromineHCID 20322217Ethyl 8-acetyl-12-(acetyloxy)heptadecanoate

Product 1

HCID 21397377Ethyl 8-acetyl-12-(acetyloxy)-8-bromoheptadecanoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

Bromine (16.7 g., 0.104 mole) dissolved in carbon tetrachloride (100 ml.) is added dropwise to a stirred solution of ethyl 8-acetyl-12-acetoxyheptadecanoate (Example 1, Step C) (37.4 g., 0.094 mole) in carbon tetrachloride (200 ml.) during one hour. The solvent is distilled in vacuo. The residual oil is dissolved in ether and washed with dilute sodium bicarbonate, water and brine and dried over sodium sulfate. Evaporation of the ether leaves the crude bromo ester as a yellow oil weighing 43 g. It is purified by column chromatography on silica gel with benzene as the eluant. This procedure serves to separate the desired bromo ester from a small amount of a by-product, ethyl 8-bromoacetyl-8-bromo-12-acetoxyheptadecanoate. Ethyl 8-acetyl-8-bromo-12-acetoxyheptadecanoate is thus obtained as a pale yellow oil weighing 12.7 g. (28%.

Workup

  1. distillationThe solvent is distilled in vacuo
  2. dissolutionThe residual oil is dissolved in ether
  3. washwashed with dilute sodium bicarbonate, water and brine
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of the ether
  6. customleaves the crude bromo ester as a yellow oil
  7. customIt is purified by column chromatography on silica gel with benzene as the eluant
  8. customto separate the desired bromo ester from a small amount of a by-product, ethyl 8-bromoacetyl-8-bromo-12-acetoxyheptadecanoate

Sources & evidence

ORD record
ord-e3eac75c10db4217832b64d08d4ed7ec
Source dataset
uspto-grants-1977_11
Patent number
US04059602

Reaction notes

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