Methyl iodide → 1-Chloro-5-(1,1-dimethylethyl)-2-methoxy-3-nitrobenzene

HRID 2075579Notes

Reaction equation

HRID 2075579 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([OH:14])=[C:7]([Cl:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:16]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[C:1]([C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([O:14][CH3:16])=[C:7]([Cl:15])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 267494-tert-Butyl-2-chloro-6-nitrophenol

Product 1

HCID 574185481-Chloro-5-(1,1-dimethylethyl)-2-methoxy-3-nitrobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
65 °C

Procedure

4-tert-Butyl-2-chloro-6-nitro-phenol (0.214 g, 0.934 mmol) was dissolved in 3 mL acetone and K2CO3 (0.65 g, 4.7 mmol) and MeI (0.58 mL, 9.3 mmol) were added. The reaction was stirred at 65° C. overnight, after which the solvent was removed under reduced pressure. The residue was taken up in DCM, the organic layer was washed with water, dried over MgSO4 and concentrated to yield 0.15 g of target product.

Workup

  1. customafter which the solvent was removed under reduced pressure
  2. washthe organic layer was washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto yield 0.15 g of target product

Sources & evidence

ORD record
ord-59e2c025948a4be7afef2b6e5f70268a
Source dataset
uspto-grants-2011_04
Patent number
US07919617B2

Reaction notes

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