Hydrogen Bromide → HCID 68451988, compound

HRID 2355109Notes

Reaction equation

HRID 2355109 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[O:17][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:15][CH:14]=1)[CH:7]=[CH:6]2.Br>C(O)(=O)C>[C:18]1([C:16]2[O:17][C:13]([C:8]3[CH:9]=[C:10]4[C:5](=[CH:6][CH:7]=3)[CH:4]=[C:3]([OH:2])[CH:12]=[CH:11]4)=[CH:14][N:15]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 68453974HCID 68453974, compound

Product 1

HCID 68451988HCID 68451988, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of 5-(6-methoxy-2-naphthyl)-2-phenyl-1,3-oxazole (433 mg, 1.44 mmol), prepared in the previous step, in 20 mL of glacial acetic acid plus 12 mL of 48% aqueous HBr was stirred under nitrogen at 120° C. for 3 h. The volatiles were removed under reduced pressure. The residue was taken up in 10% methanol in methylene chloride and then made basic by the addition of an excess of 5% NaHCO3. The layers were separated and the aqueous layer extracted three times with methylene chloride. The combined extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give 6-(2-phenyl-1,3-oxazol-5-yl)-2-naphthol (398 mg, 96%) as a light brown solid, mp 235-238° C. Elemental Analysis for C19H13NO2: Calc'd: C, 79.43; H, 4.56; N, 4.87. Found: C, 78.39; H, 4.76; N, 4.71.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. additionmade basic by the addition of an excess of 5% NaHCO3
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted three times with methylene chloride
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-bf0f938866ca4cc883a54a75a8814ffe
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

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