p-Fluoronitrobenzene → 5-[(4-Nitrophenyl)oxy]-1,3-dihydro-2-benzofuran

HRID 716823Notes

Reaction equation

HRID 716823 reaction equation
[CH2:1]1[C:5]2[CH:6]=[CH:7][C:8]([OH:10])=[CH:9][C:4]=2[CH2:3][O:2]1.F[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N+:18]([C:15]1[CH:16]=[CH:17][C:12]([O:10][C:8]2[CH:7]=[CH:6][C:5]3[CH2:1][O:2][CH2:3][C:4]=3[CH:9]=2)=[CH:13][CH:14]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 111477471,3-Dihydro-5-isobenzofuranol2×

Product 1

HCID 710901375-[(4-Nitrophenyl)oxy]-1,3-dihydro-2-benzofuranYield 97.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1,3-dihydro-2-benzofuran-5-ol (Intermediate 73, 100 mg, 0.734 mmol), 1-fluoro-4-nitrobenzene (109 mg, 0.771 mmol) and potassium carbonate (508 mg, 3.67 mmol) in acetonitrile (10 ml) was stirred under argon at 100° C. in a closed vial for 2 hours. The solid was filtered and washed with dichloromethane. The organic phase was concentrated under vacuum to afford title compound (184 mg, 96% yield)

Workup

  1. filtrationThe solid was filtered
  2. washwashed with dichloromethane
  3. concentrationThe organic phase was concentrated under vacuum

Sources & evidence

ORD record
ord-db6b7c0a22c94455922008a6d826e0e4
Source dataset
uspto-grants-2015_11
Patent number
US09193704B2

Reaction notes

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