Water → 2-Bromo-1-methoxy-4-(trifluoromethoxy)benzene

HRID 1420807Notes

Reaction equation

HRID 1420807 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].[C:14](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O.C(OCC)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][CH3:14]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 215840902-Bromo-4-(trifluoromethoxy)phenol

Product 1

HCID 186690522-Bromo-1-methoxy-4-(trifluoromethoxy)benzene

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromo-4-trifluoromethoxyphenol (Description 11; 7.2 g) and potassium carbonate (11.6 g, 0.084 mol) in dimethylformamide (60 ml) was added methyl iodide (14.94 ml, 0.24 mol). The solution was stirred for 15 h. at room temperature under nitrogen whereupon water (400 ml) and diethyl ether (200 ml) were added and the organic phase washed with water (4×200 ml), saturated NaHCO3 (2×200 ml), brine (200 ml), and the solvent removed in vacuo. The residue was purified by chromatography on silica gel eluting with ethyl acetate in hexane (0-2%), to give the title compound. 1H NMR (250 MHz, CDCl3) δ7.45 (1H, d, J 2.8 Hz), 7.16 (1H, dd, J 9.0, 2.8 Hz), 6.88 (1H, d, J 9.0 Hz), and 3.90 (3H, s).

Workup

  1. additionwere added
  2. washthe organic phase washed with water (4×200 ml), saturated NaHCO3 (2×200 ml), brine (200 ml)
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by chromatography on silica gel eluting with ethyl acetate in hexane (0-2%)

Sources & evidence

ORD record
ord-f7c83510f6724a659a3ebc48a3185b33
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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