Hydrogen Bromide → HCID 68452159, compound

HRID 2355112Notes

Reaction equation

HRID 2355112 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:30]=[CH:29][CH:28]=[CH:27][C:8]=2[C:9]=1[C:10]1[O:11][C:12]([C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:25]C)[CH:21]=3)[CH:16]=2)=[CH:13][N:14]=1)[CH2:2][CH2:3][CH3:4].Br>C(O)(=O)C>[CH2:1]([C:5]1[O:6][C:7]2[CH:30]=[CH:29][CH:28]=[CH:27][C:8]=2[C:9]=1[C:10]1[O:11][C:12]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[CH:21]=[C:20]([OH:25])[CH:19]=[CH:18]3)=[CH:13][N:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 68451238HCID 68451238, compound

Product 1

HCID 68452159HCID 68452159, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of 2-(2-butyl-1-benzofuran-3-yl)-5-(6-methoxy-2-naphthyl)-1,3-oxazole (1.82 g, 4.58 mmol), prepared in the previous step, in 85 mL of glacial acetic acid plus 50 mL of 48% aqueous HBr was stirred under nitrogen at 120° C. for 4 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-(2-butyl-1-benzofuran-3-yl)-1,3-oxazol-5-yl]-2-naphthol (1.49 g, 85%) as a pale yellow solid, mp 184-186° C. Elemental Analysis for C25H21NO3Calc'd: C, 78.31; H, 5.52; N, 3.65. Found: C, 77.35; H, 5.39; N, 3.48

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-3cd237308e38431d8762d80cb8e86976
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

Loading…