HCID 18614249, compound → HCID 18614165, compound

HRID 1265160Notes

Reaction equation

HRID 1265160 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 1M 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 1M 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-eab1aa22e9d3436dbfe1716068183a55
Source dataset
uspto-grants-2003_04
Patent number
US06545018B2

Reaction notes

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