Methyl iodide → 2-Bromo-1-methoxy-4-(trifluoromethoxy)benzene

HRID 1417526Notes

Reaction equation

HRID 1417526 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[OH:13].IC.[C:16]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:11])([F:12])[F:10])[CH:5]=[CH:4][C:3]=1[O:13][CH3:16]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 215840902-Bromo-4-(trifluoromethoxy)phenol

Product 1

HCID 186690522-Bromo-1-methoxy-4-(trifluoromethoxy)benzeneYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 608 mg (2.4 mmol) of 2-bromo-4-trifluoromethoxyphenol, 0.35 mL (5.6 mmol) of iodomethane and 775 mg (5.6 mmol) of K2CO3 in 2 mL of DMF was stirred at rt for 2.5 h. The reaction mixture was partitioned between 100 mL of hexanes and 100 mL of H2O and the layers were separated. The organic layer was washed with 2×100 mL of H2O, dried over MgSO4 and concentrated in vacuo. Flash chromatography on 25 g of silica gel using hexanes as the eluant afforded 579 mg (89%) of the title compound as an oil. 1H NMR (400 MHz, CDCl3): δ 3.91 (s, 3H), 6.88 (d, J=9.2, 1H), 7.15-7.18 (m, 1H), 7.45 (app d, J=3.2, 1H).

Workup

  1. customThe reaction mixture was partitioned between 100 mL of hexanes and 100 mL of H2O
  2. customthe layers were separated
  3. washThe organic layer was washed with 2×100 mL of H2O
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-102bf85916014bf6b1cd34f706bdd427
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

Loading…