Potassium Carbonate → 2-Methyl-5-(2-methyl-4-nitrophenoxy)benzo[d]oxazole

HRID 240540Notes

Reaction equation

[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:5]=2[N:6]=1.F[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:14]=1[CH3:22].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([O:11][C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:14]=3[CH3:22])=[CH:7][C:5]=2[N:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

2-Methylbenzo[d]oxazol-5-ol (0.86 g, 5.77 mmol), 1-fluoro-2-methyl-4-nitrobenzene (0.98 g, 6.34 mmol) and K2CO3 (1.59 g, 11.53 mmol) were combined in DMF and heated to 50° C. for 16 hours. The reaction mixture was cooled to room temperature and poured into ice water. The mixture was extracted with ethyl acetate (3×). The combined organics were washed with brine, dried, and concentrated under reduced pressure. The residue was chromatographed (20% to 40% ethyl acetate in hexanes) to provide the product (0.671 g, 41%) as yellow solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionThe mixture was extracted with ethyl acetate (3×)
washThe combined organics were washed with brine
customdried
concentrationconcentrated under reduced pressure
customThe residue was chromatographed (20% to 40% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-c45fc1bafc4e4b1a99f66d357c88cc93
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648087B2

Reaction notes

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