Methanol → 1-Chloro-4-methoxy-2-methyl-5-nitrobenzene

HRID 1773500Notes

Reaction equation

HRID 1773500 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[Cl:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([OH:16])=[C:11]([N+:17]([O-:19])=[O:18])[CH:10]=1.C(N(C(C)C)CC)(C)C.CO>C(O)(=O)C.CCCCCC>[Cl:8][C:9]1[CH:10]=[C:11]([N+:17]([O-:19])=[O:18])[C:12]([O:16][CH3:1])=[CH:13][C:14]=1[CH3:15]

Participants

7

Reactant 4

HCID 887MethanolHCID 235324-Chloro-5-methyl-2-nitrophenolHCID 81531DiisopropylethylamineHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 158645661-Chloro-4-methoxy-2-methyl-5-nitrobenzeneYield 99.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 8058HexaneSolvent

Procedure

A solution of (trimethylsilyl)diazomethane (2.0 M in hexane, 13.3 mL, 26.6 mmol) was added to a mixture of 4-chloro-5-methyl-2-nitro-phenol (1.0 g, 5.33 mmol) and diisopropylethylamine (1.04 mL, 6.13 mmol) in a mixture of anhydrous methanol and anhydrous acetonitrile (1/1, 50 mL) and the reaction mixture was stirred for 1 hour. Glacial acetic acid (5 drops) was then added and the resulting mixture was evaporated under reduced pressure. The residue was partitioned between diethyl ether (100 mL) and water (50 mL); the organic layer was separated, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to afford 1.07 g of 1-chloro-4-methoxy-2-methyl-5-nitro-benzene as a light orange solid without further purifications.

Workup

  1. customthe resulting mixture was evaporated under reduced pressure
  2. customThe residue was partitioned between diethyl ether (100 mL) and water (50 mL)
  3. customthe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-81901a21fb5347a79d48bb912fed813c
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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