Iodoethane → 4-Bromo-2-ethoxy-1-fluorobenzene

HRID 1515506Notes

Reaction equation

HRID 1515506 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([OH:8])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH2:16](I)[CH3:17]>CN(C=O)C.CCOCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([O:8][CH2:16][CH3:17])[CH:7]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 183421Phenol, 5-bromo-2-fluoro-

Product 1

HCID 598380294-Bromo-2-ethoxy-1-fluorobenzeneYield 77%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 7A (4.4 g, 23 mmol) and K2CO3 (6.4 g, 46 mmol) in DMF (30 mL) was added ethyl iodide (2.49 mL, 31 mmol) at rt. The mixture was heated at 50° C. for 2.0 h. After cooling to rt, it was diluted with ether, washed with water and brine, dried over MgSO4. The crude residue was purified by flash column chromatography (EtOAc:hexanes=1:5) to give 3.86 g (77%) of 9A as viscous oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.47 (m, 3H) 4.00 (m, 2H) 6.96-7.08 (m, 3H).

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 (EtOAc:hexanes=1:5)

Sources & evidence

ORD record
ord-29f817352b7f46d6af69d185169f6388
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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