Ethyl Acetate → HCID 136073675, compound

HRID 646453Notes

Reaction equation

HRID 646453 reaction equation
[Br-:1].[Br-].[Br-].C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.[CH3:37][O:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]2[C:46]([CH3:58])=[N:47][O:48][C:49]=2[C:50]2[CH:55]=[CH:54][C:53]([OH:56])=[CH:52][C:51]=2[OH:57])=[CH:41][CH:40]=1.C(OCC)(=O)C>ClCCl>[Br:1][C:54]1[CH:55]=[C:50]([C:49]2[O:48][N:47]=[C:46]([CH3:58])[C:45]=2[C:42]2[CH:41]=[CH:40][C:39]([O:38][CH3:37])=[CH:44][CH:43]=2)[C:51]([OH:57])=[CH:52][C:53]=1[OH:56]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 53442637BenzyltrimethylammoniumtribromideHCID 135650270HCID 135650270, compound

Product 1

HCID 136073675HCID 136073675, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyltrimethylammonium tribromide (3.95 g, 10 mmol) was added portion-wise to an ice cooled suspension of 4-[4-(4-methoxy-phenyl)-3-methyl-isoxazol-5-yl]-benzene-1,3-diol (Example 1) (2.95 g, 10 mmol) in dichloromethane (50 ml) and the mixture stirred for ˜60 mins, at room temperature. Ethyl acetate (300 ml) was added and the mixture washed with water (3×200 ml) and saturated aqueous sodium chloride solution (50 ml). The solution was dried over anhydrous magnesium sulphate and concentrated to give a pale brown solid. Crude product was purified by column chromatography, on silica, eluting with ethyl acetate/hexane (1:2), to give 4-bromo-6-[4-(4-methoxy-phenyl)-3-methyl-isoxazol-5-yl]-benzene-1,3-diol as a white solid, dried in vacuo, (3.42 g)

Workup

  1. temperaturecooled
  2. washthe mixture washed with water (3×200 ml) and saturated aqueous sodium chloride solution (50 ml)
  3. dry with materialThe solution was dried over anhydrous magnesium sulphate
  4. concentrationconcentrated
  5. customto give a pale brown solid
  6. customCrude product was purified by column chromatography, on silica
  7. washeluting with ethyl acetate/hexane (1:2)

Sources & evidence

ORD record
ord-eb462c64aff442d9acfe25fbb1955136
Source dataset
uspto-grants-2010_04
Patent number
US07705027B2

Reaction notes

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