5-Fluoro-2-nitrophenol → HCID 21921907, compound

HRID 1245082Notes

Reaction equation

HRID 1245082 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.[OH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22]C)=[O:21])=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[OH:8][C:6]1[CH:7]=[C:2]([CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10])[O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium CarbonateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 21921907HCID 21921907, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To 4.0 g (4.0 mmol) of resin-bound 5-fluoro-2-nitro-phenol prepared as generally described in Example 37 in 8.0 mL of DMF were added 1.34 g (8.0 mmol) of methyl 4-hydroxyphenylacetate, and 1.20 g (8.0 mmol) of K2CO3. The mixture was heated to 110° C. for 12 h. The resin was washed with H2O, DMF, MeOH, DCM three times of each, and was hydrolyzed by LiOH/H2O/THF/ethanol at rt for 12 h to give the resin-bound [4-(3-hydroxy-4-nitro-phenoxy)-phenyl]-acetic acid.

Workup

  1. washThe resin was washed with H2O, DMF, MeOH, DCM three times of each, and

Sources & evidence

ORD record
ord-fdaaab80309e427fb28a4d370b60895c
Source dataset
uspto-grants-2006_10
Patent number
US07122580B2

Reaction notes

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