Bromine → HCID 10399369, compound

HRID 1110356Notes

Reaction equation

HRID 1110356 reaction equation
[C:1]([CH:3]([CH3:13])[CH2:4][CH:5]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=O)#[N:2].[Br:14]Br>C(O)(=O)C>[Br:14][C:1]1[N:2]=[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:5]2=[CH:4][C:3]=1[CH3:13]

Participants

4

Reactant 2

HCID 24408BromineHCID 15007047HCID 15007047, compound

Product 1

HCID 10399369HCID 10399369, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
15 °C

Procedure

The product of step (a) (88 g, 0.5 m) in acetic acid (11) was treated with bromine (26 ml, 0.5 m) over 15 minutes, maintaining an internal temperature of ca, 15° C. The mixture was allowed to warm to room temperature overnight. The solvent was evaporated off under reduced pressure and the residue partitioned between water and diisopropyl ether. The organic phase was dried (MgSO4) and evaporated to give a residue which on recrystallising from hexane gave the title compound as white needles, mp 68-70.

Workup

  1. temperatureto warm to room temperature overnight
  2. customThe solvent was evaporated off under reduced pressure
  3. customthe residue partitioned between water and diisopropyl ether
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated
  6. customto give a residue which
  7. customon recrystallising from hexane

Sources & evidence

ORD record
ord-b32cf038f5ba434e8423d29fc05043a2
Source dataset
uspto-grants-1990_12
Patent number
US04975431

Reaction notes

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