p-Fluoronitrobenzene → HCID 67960136, compound

HRID 527508Notes

Reaction equation

HRID 527508 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([OH:16])[C:10]=2[CH2:9][O:8]1.F[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1>CN(C)C=O>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([O:16][C:15]2[C:10]3[CH2:9][O:8][CH2:7][C:11]=3[CH:12]=[CH:13][CH:14]=2)=[CH:19][CH:20]=1)([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 67958682HCID 67958682, compound2×

Product 1

HCID 67960136HCID 67960136, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of potassium carbonate (670 mg, 4.85 mmol), 1,3-dihydro-2-benzofuran-4-ol (Intermediate 2, 110 mg) and 1-fluoro-4-nitrobenzene (114 mg, 0.808 mmol) in N,N-dimethylformamide (DMF) (5 ml) was heated under microwave irradiation at 100° C. for 3×30 minutes. The mixture was concentrated. 2 ml of water were added and then dichloromethane. The phases were separated and the aqueous phase was extracted twice with dichloromethane. The organic phase was dried over sodium sulphate and concentrated under vacuum to afford the title compound, which was directly used in the next step.

Workup

  1. concentrationThe mixture was concentrated
  2. addition2 ml of water were added
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted twice with dichloromethane
  5. dry with materialThe organic phase was dried over sodium sulphate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9e8458815d5549d894145acec3e77f8a
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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