Potassium Carbonate → HCID 58485966, compound

HRID 655315Notes

Reaction equation

HRID 655315 reaction equation
[F:1][C:2]1[C:3]([F:12])=[CH:4][C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1.Br[CH:14]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=1)[CH3:15].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CC(OC)(C)C>[F:1][C:2]1[C:3]([F:12])=[CH:4][C:5]2[O:9][C:8](=[O:10])[N:7]([CH:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=3)[CH3:15])[C:6]=2[CH:11]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 115356375,6-difluorobenzo[d]oxazol-2(3H)-oneHCID 229178381-(1-Bromoethyl)-3-nitrobenzene

Product 1

HCID 58485966HCID 58485966, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
60 °C

Procedure

500 mg (2.9 mmol) of 5,6-difluoro-3H-benzoxazol-2-one, 672 mg (2.9 mmol) of (1-bromoethyl)-3-nitrobenzene and 1.58 g (11.4 mmol) of potassium carbonate are suspended in 6 ml of acetonitrile, and the mixture is stirred at 60° C. for 6 h. The mixture is subsequently diluted with 30 ml of MTBE, washed with 3×20 ml of H2O, dried over sodium sulfate and evaporated to dryness. The crude product is purified by column chromatography on silica gel.

Workup

  1. washwashed with 3×20 ml of H2O
  2. dry with materialdried over sodium sulfate
  3. customevaporated to dryness
  4. customThe crude product is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ff1007f86899409681298a51883ce4ec
Source dataset
uspto-grants-2011_12
Patent number
US08071593B2

Reaction notes

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