Methyl iodide → 5-Bromo-1-chloro-3-ethyl-2-methoxy-benzene

HRID 858772Notes

Reaction equation

HRID 858772 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].CI.[Br:9][C:10]1[CH:15]=[C:14]([CH2:16][CH3:17])[C:13](O)=[C:12]([Cl:19])[CH:11]=1>CN(C=O)C>[Br:9][C:10]1[CH:15]=[C:14]([CH2:16][CH3:17])[C:13]([O:4][CH3:1])=[C:12]([Cl:19])[CH:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 587626844-Bromo-2-chloro-6-ethylphenol

Product 1

HCID 587623425-Bromo-1-chloro-3-ethyl-2-methoxy-benzeneYield 904.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (3.9 g, 28 mmol) followed by methyl iodide (0.58 mL, 9.3 mmol) were added to a solution of 4-bromo-2-chloro-6-ethyl-phenol (2.2 g, 9.3 mmol) in DMF (10 mL). The mixture was stirred for 20 hours and then partitioned between 1N HCl and EtOAc. The organic layers were washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The crude yellow oil was purified by flash column chromatography (0% to 3% EtOAc in hexanes) to give the desired product (21 g, 91%) 1H NMR (400 MHz, CDCl3): δ 1.22 (t, J=7.6 Hz, 3 H), 2.66 (q, J=7.6 Hz, 2 H), 3.82 (s, 3 H), 7.22 (s, 1 H), 7.37 (s, 1 H).

Workup

  1. custompartitioned between 1N HCl and EtOAc
  2. washThe organic layers were washed with saturated NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude yellow oil was purified by flash column chromatography (0% to 3% EtOAc in hexanes)

Sources & evidence

ORD record
ord-bc8feec1ab1e4bcd8b09fc21f8f0b0d0
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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