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

HRID 1420683Notes

Reaction equation

HRID 1420683 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 (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 hours at room temperature under nitrogen whereupon water (400 ml) and diethyl ether (200 ml) were added. The organic phase was 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; δH (250 MHz, CDCl3) 7.45 (1H, d, J 2.8Hz, 3-H), 7.16 (1H, dd, J 9.0, 2.8Hz, 5-H), 6.88 (1H, d, J 9.0Hz, 6-H), 3.90 (3H, s, ArOCH3).

Workup

  1. additionwere added
  2. washThe organic phase was 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-179a9c8fea92485ba7ccfefb22d9fcdd
Source dataset
uspto-grants-2000_06
Patent number
US06071928

Reaction notes

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