Dimethylformamide → HCID 11106773, compound

HRID 2108666Notes

Reaction equation

HRID 2108666 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[OH:13])=[CH:4][CH:3]=1.[CH3:16]N(C=O)C.C(=O)([O-])[O-].[K+].[K+].CI>C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[O:13][CH3:16])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2584312-[(4-Fluorophenyl)methyl]phenol

Product 1

HCID 11106773HCID 11106773, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(4-fluorobenzyl)phenol (4.51 gm, 22.41 mmol), DMF (60 mL), potassium carbonate (7.78 gm, 56.02 mmol) and methyl iodine (1.67 mL, 26.81 mmol) was stirred at rt for 16 h. The reaction was poured into 150 mL ethyl acetate, filtered, washed 3× with 50 mL H20, 1× with 100 m]L brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford 2-(4-fluorobenzyl)anisole (4.27 gm, 88%); 1H NMR (200 MHz, DMSO-d6): δ 7.11(m, 7H), 3.88(s, 2H), 3.76(s, 3H); TLC conditions: Uniplate silica gel, 250 microns; methylene chloride-hexanes (1:1); Rf=0.64.

Workup

  1. filtrationfiltered
  2. washwashed 3× with 50 mL H20, 1× with 100 m]L brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5f9182a93c8f4f879419c5e9cde2881f
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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