Iodoethane → 4-Bromo-1-chloro-2-ethoxybenzene

HRID 1438123Notes

Reaction equation

HRID 1438123 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[OH:9].C([O-])([O-])=O.[K+].[K+].[CH2:16](I)[CH3:17]>CN(C=O)C.CCOCC>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:9][CH2:16][CH3:17])[CH:4]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 8203925-Bromo-2-chlorophenol

Product 1

HCID 509981874-Bromo-1-chloro-2-ethoxybenzeneYield 99%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 2-chloro-5-bromophenol (WO98/003464 which is incorporated herein by reference, 3.43 g, 16.5 mmol) and K2CO3 (4.57 g, 33.0 mmol) in DMF (20 mL) was added ethyl iodide (1.78 mL, 22.3 mmol) at rt. The mixture was heated at 55° C. for 3.0 h. After cooling to rt, the reaction was diluted with ether, washed with water and brine, and dried over MgSO4. The crude residue was purified by flash column chromatography to give 3.85 g (99%) of 31A as viscous oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.48 (t, J=7.03 Hz, 3H) 4.08 (d, J=7.03 Hz, 2H) 7.03 (m, 2H) 7.22 (d, J=6.15 Hz, 2H).

Workup

  1. temperatureAfter cooling to rt
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. customThe crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-344de20d8a2042ac991181a546e3b574
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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