Dichloromethane → 2-Bromooctadecanal

HRID 260526Notes

Reaction equation

HRID 260526 reaction equation
[CH:1](=[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][CH2:16][CH2:17][CH3:18].ClCCl.O1CCOCC1.[Br:29]Br>O>[Br:29][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][CH2:16][CH2:17][CH3:18])[CH:1]=[O:19]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 12533OctadecanalHCID 24408BromineHCID 312751,4-Dioxane

Product 1

HCID 5372552-BromooctadecanalYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 21 parts of octadecanal in 65 parts of dichloromethane and 50 parts of 1,4-dioxane there were added dropwise 34.1 parts of bromine. After stirring for 4 hours at room temperature, the reaction mixture was poured into 250 parts of water. The product was extracted with dichloromethane and the extract was dried, filtered and evaporated, yielding 28 parts (95%) of 2-bromooctadecanal (interm. 1).

Workup

  1. extractionThe product was extracted with dichloromethane
  2. customthe extract was dried
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-4461cb09591f42b5ba3fa0938bb77d41
Source dataset
uspto-grants-1996_06
Patent number
US05527915

Reaction notes

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