Phenyltrimethylammonium bromide dibromide → HCID 23016506, compound

HRID 417821Notes

Reaction equation

HRID 417821 reaction equation
[Br-:1].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.[C:34]([C:39]1[CH:40]=[C:41]([CH:46]=[CH:47][CH:48]=1)[C:42]([O:44][CH3:45])=[O:43])(=[O:38])[CH:35]([CH3:37])[CH3:36]>O1CCCC1>[CH3:45][O:44][C:42]([C:41]1[CH:40]=[C:39]([C:34](=[O:38])[C:35]([Br:1])([CH3:37])[CH3:36])[CH:48]=[CH:47][CH:46]=1)=[O:43]

Participants

4

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 23016502HCID 23016502, compound

Product 1

HCID 23016506HCID 23016506, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.8 g of phenyltrimethylammonium tribromide was added to a mixture comprising 1.5 g of the crude product of methyl m-isobutyrylbenzoate obtained in the above step (3) and 20 ml of tetrahydrofuran, and followed by a reaction at room temperature overnight. After completion of the reaction, the precipitated crystal was separated by filtration, then tetrahydrofuran was distilled off. The residue was dissolved in ethyl acetate, then washed with a saturated sodium chloride aqueous solution, followed by drying over anhydrous sodium sulfate. Then, concentration under reduced pressure was carried out, and then, rough purification was carried out by silica gel column chromatography to obtain 0.27 g of crude 3′-methoxycarbonyl-2-bromo-2-methylpropiophenone. The NMR spectrum data of this product were as follows.

Workup

  1. customfollowed by a reaction at room temperature overnight
  2. customAfter completion of the reaction
  3. customthe precipitated crystal was separated by filtration
  4. distillationtetrahydrofuran was distilled off
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with a saturated sodium chloride aqueous solution
  7. dry with materialby drying over anhydrous sodium sulfate
  8. concentrationThen, concentration under reduced pressure
  9. customrough purification

Sources & evidence

ORD record
ord-060a11f4f3f14775bac10946c8a52ed6
Source dataset
uspto-grants-2012_01
Patent number
US08093241B2

Reaction notes

Loading…