Hydrogen Bromide → HCID 68451974, compound

HRID 2355130Notes

Reaction equation

HRID 2355130 reaction equation
[CH2:1]([C:8]1[O:9][C:10]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:23]C)[CH:19]=3)[CH:14]=2)=[CH:11][N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br>C(O)(=O)C>[CH2:1]([C:8]1[O:9][C:10]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[CH:19]=[C:18]([OH:23])[CH:17]=[CH:16]3)=[CH:11][N:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 260Hydrogen Bromide2×HCID 68451835HCID 68451835, compound

Product 1

HCID 68451974HCID 68451974, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Benzyl-5-(6-methoxy-2-naphthyl)-1,3-oxazole (2.53 g, 7.59 mmol), prepared in the previous step, in 25 mL of glacial acetic acid plus 10 mL of 48% aqueous HBr was stirred under nitrogen at 120° C. for 10 h. After cooling to room temperature the HBr and the acetic acid were removed under reduced pressure. The residue was taken up in 500 mL of 90% CH3OH/CH2Cl2, extracted three times with a total of 250 mL of 5% NaHCO3, dried (MgSO4), filtered and the solvent was removed under reduced pressure to give 6-(2-benzyl-1,3-oxazol-5-yl)-2-naphthol (2.24 g, 98%) as a brown solid, mp 200-202° C. Elemental Analysis for C20H15NO2 Calc'd: C, 79.72; H, 5.02; N, 4.65. Found: C, 78.63; H, 5.15; N, 4.44.

Workup

  1. customthe acetic acid were removed under reduced pressure
  2. extractionextracted three times with a total of 250 mL of 5% NaHCO3
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1929c8a62b2d45bbb0bb81395caddfb7
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

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