Cesium carbonate → 5-(2-Methyl-4-nitrophenoxy)benzo[d]oxazole

HRID 240576Notes

Reaction equation

HRID 240576 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([OH:10])=[CH:9][C:4]=2[N:3]=[CH:2]1.F[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=1[CH3:21].C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:21][C:13]1[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:12]=1[O:10][C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH:2]=[N:3][C:4]=2[CH:9]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-HCID 190201831,3-Benzoxazol-5-ol

Product 1

HCID 669369305-(2-Methyl-4-nitrophenoxy)benzo[d]oxazoleYield 56.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of benzo[d]oxazol-5-ol (1.50 g, 11.10 mmol) and 1-fluoro-2-methyl-4-nitrobenzene (1.89 g, 12.21 mmol) in DMF was added cesium carbonate (1.81 g, 5.55 mmol) and potassium carbonate (2.30 g, 16.65 mmol). After heating to 50° C. for 16 hours, the mixture was poured into ice water and extracted with ethyl acetate (3×). The combined organics were washed with brine, dried, and concentrated under reduced pressure. The residue was chromatographed (30% ethyl acetate in hexanes) to provide the product (1.69 g, 56%) as white solid.

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organics were washed with brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-312f136f09e2463eafb56025af1e0d5f
Source dataset
uspto-grants-2014_02
Patent number
US08648087B2

Reaction notes

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