Bromine → 3-Bromo-1-dodecylazacycloheptan-2-one

HRID 845101

Reaction equation

HRID 845101 reaction equation
[CH2:1]([N:13]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:14]1=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].P(Cl)(Cl)(Cl)(Cl)Cl.[Br:27]Br>C(Cl)(Cl)Cl>[Br:27][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][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])[C:14]1=[O:20]

Participants

5

Reactant 3

HCID 24408BromineHCID 24819Phosphorus pentachlorideHCID 42981Laurocapram

Product 1

HCID 141826953-Bromo-1-dodecylazacycloheptan-2-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a cold solution of 107 g (0.38 mol) of 1-dodecylazacycloheptan-2-one, in CHCl3 was added 159.7 g (0.77 mol) of PCl5, keeping the temperature between 1°-4° C. After 2 hours, a solution of 123.3 g (0.77 mol) of bromine in CHCl3 was added, and the mixture was stirred for 18 hours at room temperature. After removing the solvent and excess bromine by vacuum distillation, the residue was dissolved in CH2Cl2, washed with sat. Na2S2O5, dried over MgSO4, and concentrated in vacuo to give a crude oil. Purification by flash chromatography (silica gel; 1:1 ether/petroleum ether V/V) gave pure product.

Workup

  1. custombetween 1°-4° C
  2. customAfter removing the solvent and excess bromine
  3. distillationby vacuum distillation
  4. dissolutionthe residue was dissolved in CH2Cl2
  5. washwashed with sat. Na2S2O5
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customto give a crude oil
  9. customPurification by flash chromatography (silica gel; 1:1 ether/petroleum ether V/V)
  10. customgave pure product

Sources & evidence

ORD record
ord-24c5b0f902134d598ede491cde24c195
Source dataset
uspto-grants-1988_07
Patent number
US04755535

Linked notes

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