Bromine → 2-Bromoisooctadecanoyl chloride

HRID 1638392Notes

Reaction equation

HRID 1638392 reaction equation
[C:1]([Cl:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17].[Br:21]Br>>[Br:21][CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH3:17])[CH3:18])[C:1]([Cl:20])=[O:19]

Participants

3

Reactant 2

HCID 24408Bromine3×HCID 118402Heptadecanoyl chloride, 16-methyl-

Product 1

HCID 197887732-Bromoisooctadecanoyl chloride

Procedure

Isooctadecanoyl chloride prepared as described in Example 5 (20.2 g) was stirred and heated to 100° and illuminated with a tungsten lamp (100 watts) whilst bromine (10.7 g) was added dropwise during 1.5 hours. Heating and stirring under illumination were continued and further additions of bromine were made until after 10 hours and the addition of a further 6 g of bromine, 95% of the starting material was shown by gas chromatography to be completely reacted. Excess bromine and hydrobromic acid were removed by applying vacuum (20 mm of mercury) to the heated liquid. The 2-bromoisooctadecanoyl chloride thus obtained was cooled and treated with 1,2,4-triazole (9.0 g) and drowned into water and extracted with petroleum ether (b.p. 60°-80° ). The organic solution was separated and washed with aqueous hydrochloric acid (2M) and water, and the solvent was distilled leaving 1-(2'-bromoiso- octadecanoyl)-1,2,4-triazole (25.3 g) as a pale brown oil. The nuclear magnetic resonance spectrum of the product as a solution in deuterated chloroform was compared with that of the product of Example 5, confirming that absorption at delta 3.4 ppm from tetramethylsilane, associated with a proton in the 2'-position of the side chain, had vanished. This compound was evaluated as an extractant for copper by the procedure of Example 1 and the results are presented in Table 1. The results show that the compound is a slightly "weaker" ligand than the products of Examples 1-7, and that it transfers only a small amount of acid.

Workup

  1. temperatureheated to 100°
  2. additionwas added dropwise during 1.5 hours
  3. temperatureHeating
  4. stirringstirring under illumination
  5. customafter 10 hours
  6. customto be completely reacted
  7. customExcess bromine and hydrobromic acid were removed

Sources & evidence

ORD record
ord-88410defd12845f8b43b74dedb6bec2a
Source dataset
uspto-grants-1989_11
Patent number
US04879388

Reaction notes

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