HCID 18614249, compound → HCID 18614165, compound

HRID 2268125Notes

Reaction equation

HRID 2268125 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([N+:25]([O-])=O)[CH:22]=[C:21]([CH3:28])[C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH:6]=1>C(O)(=O)C.C(OCC)(=O)C.[Zn]>[NH2:25][C:23]1[CH:22]=[C:21]([CH3:28])[C:3]([O:4][C:5]2[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH:6]=2)=[C:2]([Cl:1])[CH:24]=1

Participants

5

Reactant 1

HCID 18614249HCID 18614249, compound

Product 1

HCID 18614165HCID 18614165, compoundYield 97.2%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a warm (100° C.) solution of 4-(2-chloro-6-methyl-4-nitro-phenoxy)-2-(4-fluorophenoxymethyl)-phenol (100 mg) in glacial acetic acid (2.5 mL) was added zinc dust (243 mg) and heating was continued for 30 min. The reaction mixture was cooled, diluted with ethyl acetate and filtered through Celite®. The filtrate was washed with 1 M aqueous sodium bicarbonate, dried over sodium sulfate, concentrated in vacuo and flashed chromatographed (30% ethyl acetate/hexanes) to afford 4-(4-amino-2-chloro-6-methyl-phenoxy)-2-(4-fluoro-phenoxymethyl)-phenol (90 mg) as a tan solid.

Workup

  1. temperatureheating
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered through Celite®
  4. washThe filtrate was washed with 1 M aqueous sodium bicarbonate
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customflashed chromatographed (30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-33d5bdd40c124c83a52499524c17c78e
Source dataset
uspto-grants-2001_12
Patent number
US06326398B1

Reaction notes

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