Sulfuric Acid → HCID 18614249, compound

HRID 1265159Notes

Reaction equation

HRID 1265159 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 1N aqueous sodium bicarbonate, extracted with ethyl acetate, the organic layer dried over sodium sulfate and concentrated in vacuo. Flash chromatography (15% ethyl acetatelhexanes) 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 1N 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-2f0e33c93b6f41f9a0609bfc685b4b51
Source dataset
uspto-grants-2003_04
Patent number
US06545018B2

Reaction notes

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