Water → HCID 21961344, compound

HRID 1017870Notes

Reaction equation

HRID 1017870 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[C:5]([CH3:18])[C:4]=1[CH3:19].C([O-])(=O)C.[Na+].[Br:25]Br.O>C(O)(=O)C>[C:13]([O:12][C:11](=[O:17])[NH:10][C:6]1[C:5]([CH3:18])=[C:4]([CH3:19])[C:3]([O:2][CH3:1])=[C:8]([Br:25])[C:7]=1[CH3:9])([CH3:14])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 517045Sodium AcetateHCID 21961339HCID 21961339, compound

Product 1

HCID 21961344HCID 21961344, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of tert-butyl 4-methoxy-2,3,6-trimethylphenylcarbamate (12.7 g, 47.9 mmol) and sodium acetate (4.72 g, 57.5 mg) in acetic acid (50 ml) was added at room temperature bromine (8.42 g, 52.7 mmol) and the resulting mixture was stirred at the same temperature for 1 hour. Water (80 ml) was added into the reaction mixture. The crystals precipitated were collected by filtration and dissolved into ethyl acetate. The solution was washed with an aqueous saturated solution of sodium hydrogen carbonate, dried on magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was crystallized from methanol to obtain 15.0 g (91% yield) of the title compound. Melting point: 159-161° C.

Workup

  1. customThe crystals precipitated
  2. filtrationwere collected by filtration
  3. dissolutiondissolved into ethyl acetate
  4. washThe solution was washed with an aqueous saturated solution of sodium hydrogen carbonate
  5. customdried on magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-a217e0ea7b4d4f5aa394338905df2d67
Source dataset
uspto-grants-2002_11
Patent number
US06479536B1

Reaction notes

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