Bromine → HCID 15296920, compound

HRID 2210882Notes

Reaction equation

HRID 2210882 reaction equation
[CH2:1]([N:13]1[N:17]=[N:16][C:15]([CH2:18][C:19]([OH:21])=[O:20])=[N:14]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Br:22]Br>C(Cl)(Cl)(Cl)Cl.C(OCC)(=O)C>[Br:22][CH:18]([C:15]1[N:16]=[N:17][N:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[N:14]=1)[C:19]([OH:21])=[O:20]

Participants

5

Reactant 2

HCID 24408BromineHCID 10661649HCID 10661649, compound

Product 1

HCID 15296920HCID 15296920, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

The 2-dodecyltetrazoleacetic acid (4.7 g, 15.8 mmol) was suspended in carbon tetrachloride (5 mL) and warmed to 45° C. The solution was diluted by dropwise addition of bromine (2.6 g, 16.3 mmol), and the mixture was further heated to reflux with stirring for 5 hours. The solution was cooled to room temperature, diluted with 50 mL of ethyl acetate, washed with brine, dried (MgSO4), and filtered. The filtrate was concentrated in vacuo to give α-bromo-2-dodecyltetrazoleacetic acid (5.3 g, 86%) as an orange colored liquid;

Workup

  1. temperaturethe mixture was further heated
  2. temperatureto reflux
  3. temperatureThe solution was cooled to room temperature
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a7bb6aab02564b88accf2d5c2c8820d6
Source dataset
uspto-grants-1995_10
Patent number
US05461049

Reaction notes

Loading…