Water → HCID 21961344, compound

HRID 2376307Notes

Reaction equation

HRID 2376307 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>[Br:25][C:8]1[C:7]([CH3:9])=[C:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[C:5]([CH3:18])=[C:4]([CH3:19])[C:3]=1[O:2][CH3:1]

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 synthesized in Reference Example 128 (12.7 g, 47.9 mmol) and sodium acetate (4.72 g, 57.5 mmol) in acetic acid (50 mL) was added bromine (8.42 g, 52.7 mmol) at room temperature and the mixture was stirred at the same temperature for 1 hour. Water (80 mL) was poured into the reaction mixture, and the precipitated crystals were collected by filtration and then dissolved in ethyl acetate. The solution was washed with a saturated sodium hydrogen carbonate solution and water, dried over magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was crystallized from methanol to obtain 15.0 g (yield 91%) of the title compound. Melting point: 159-161° C.

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. dissolutiondissolved in ethyl acetate
  3. washThe solution was washed with a saturated sodium hydrogen carbonate solution and water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-453d3c030a524b1ab355686ad8f23faa
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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