Potassium Carbonate → 2-(3-Bromo-phenyl)-5-phenyl-benzoxazole

HRID 659111

Reaction equation

HRID 659111 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:4][C:3]=1[OH:14].[Br:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19](Cl)=O.C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1.[Cl-].[Na+].O>[Br:15][C:16]1[CH:17]=[C:18]([C:19]2[O:14][C:3]3[CH:4]=[CH:5][C:6]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)=[CH:7][C:2]=3[N:1]=2)[CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 145622-Amino-4-phenylphenolHCID 74377Benzoyl chloride, 3-bromo-

Product 1

HCID 593348442-(3-Bromo-phenyl)-5-phenyl-benzoxazole

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-amino-4-phenylphenol (30) (250 mg, 1.20 mmol) and 3-bromo-benzoyl chloride (31) (265 mg, 1.20 mmol) were heated in NMP at 150° C. overnight. The reaction was cooled to ambient temperature then K2CO3 (aq) and brine were added, and the aqueous extracted with EtOAc (×5). The organic layer was washed with brine, dried (Na2SO4), and the solvent concentrated in vacuo. The crude product was purified by column chromatography eluting with a mixture of 1:1 DCM in heptane to yield the title compound. Yield: 210 mg, 49%; LC-MS tr 2.02 min; HPLC Purity: 67%; MS (ES+) m/z 350, 352 (M+H)

Workup

  1. extractionthe aqueous extracted with EtOAc (×5)
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationthe solvent concentrated in vacuo
  5. customThe crude product was purified by column chromatography
  6. washeluting with a mixture of 1:1 DCM in heptane

Sources & evidence

ORD record
ord-c064c2f3a323463bbfc766a2e457ce49
Source dataset
uspto-grants-2011_12
Patent number
US08080567B2

Linked notes

Loading…