1,2-Dichloroethane → 2-Bromo-1-(2-chloroethoxy)-4-methoxybenzene

HRID 1870501Notes

Reaction equation

HRID 1870501 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[OH:10].[Cl:11][CH2:12][CH2:13]Cl.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[O:10][CH2:13][CH2:12][Cl:11]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 14798Sodium HydroxideHCID 2973822-Bromo-4-methoxyphenol

Product 1

HCID 154539192-Bromo-1-(2-chloroethoxy)-4-methoxybenzene

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

To a solution of 2-bromo-4-methoxyphenol (20.00 g, 98.04 mmol) in 1,2-dichloroethane (50.00 mL, 0.63 mol) was added sodium hydroxide (12.00 g, 0.29 mol) and benzyltriethylammonium chloride (3.00 g) in water (150 mL). The mixture was stirred at reflux for 24 h and extracted with ethyl acetate (3×150 mL). The combined organic extracts were washed with brine and dried (Na2SO4). After removing the solvent under reduced pressure, flash chromatography (1:1 diethyl ether/hexane) of the residue gave 14.20 g (66% over two steps) of the title compound as a yellow oil: 1H NMR (250 MHz, CDCl3) d 7.09 (d, 1 H), 6.82-6.72 (m, 2 H), 4.27 (t, 2 H), 3.75 (t, 3 H), 3.71 (s, 3 H).

Workup

  1. temperatureat reflux for 24 h
  2. extractionextracted with ethyl acetate (3×150 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customAfter removing the solvent under reduced pressure, flash chromatography (1:1 diethyl ether/hexane) of the residue

Sources & evidence

ORD record
ord-0d9af05ffaf045ce973b1070680b9c46
Source dataset
uspto-grants-2000_08
Patent number
US06096897

Reaction notes

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