Sulfuric Acid → HCID 18614249, compound

HRID 2268124Notes

Reaction equation

HRID 2268124 reaction equation
[Cl:1][C:2]1[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[CH:30]=[C:29]([CH3:36])[C:3]=1[O:4][C:5]1[CH:19]=[CH:18][C:8]([O:9]COCC[Si](C)(C)C)=[C:7]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH:6]=1.C1COCC1.S(=O)(=O)(O)O>CO>[Cl:1][C:2]1[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[CH:30]=[C:29]([CH3:36])[C:3]=1[O:4][C:5]1[CH:19]=[CH:18][C:8]([OH:9])=[C:7]([CH2:20][O:21][C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8028TetrahydrofuranHCID 18614175HCID 18614175, compound

Product 1

HCID 18614249HCID 18614249, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of {2-[4-(2-chloro-6-methyl-4-nitro-phenoxy)-2-(4-fluoro-phenoxymethyl)-phenoxymethoxy]-ethyl}-trimethylsilane (280 mg) in MeOH (2.5 mL)/THF (0.2 mL) was added 6% sulfuric acid in MeOH (2.5 mL) and the resulting solution was stirred for 1 h. The reaction was quenched with 1 N aqueous sodium bicarbonate, extracted with ethyl acetate, the organic layer dried over sodium sulfate and concentrated in vacuo. Flash chromatography (15% ethyl acetate/hexanes) afforded 4-(2-chloro-6-methyl-4-nitro-phenoxy)-2-(4-fluorophen-oxymethyl)-phenol (170 mg) as a yellow semi-solid.

Workup

  1. customThe reaction was quenched with 1 N aqueous sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic layer dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6e6097174c744f77822e4c6ab58a31a4
Source dataset
uspto-grants-2001_12
Patent number
US06326398B1

Reaction notes

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