Isopropyl iodide → 1-Bromo-4-fluoro-2-[(propan-2-yl)oxy]benzene

HRID 2377801Notes

Reaction equation

HRID 2377801 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[OH:9].I[CH:11]([CH3:13])[CH3:12].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[O:9][CH:11]([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 27246002-Bromo-5-fluorophenol

Product 1

HCID 467388251-Bromo-4-fluoro-2-[(propan-2-yl)oxy]benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-Bromo-5-fluoro-phenol Compound 4a (3.0 g, 15.7 mmol), 2-iodo-propane Compound 4b (4.0 g, 23.6 mmol), K2CO3 (3.3 g, 23.6 mmol) and DMF (50 mL) were heated and stirred at 80° C. for 8 hrs. The excess DMF was removed under reduced pressure and the white residue was mixed with AcOEt (100 mL), washed with water and dried (Na2SO4). The filtered dry solution was evaporated to provide 1-bromo-4-fluoro-2-isopropoxy-benzene Compound 4c (3.48 g, 95%) as a yellowish oil.

Workup

  1. customThe excess DMF was removed under reduced pressure
  2. additionthe white residue was mixed with AcOEt (100 mL)
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. customThe filtered dry solution was evaporated

Sources & evidence

ORD record
ord-9ae1cac552b24700b9279a71ad983e1a
Source dataset
uspto-grants-2008_12
Patent number
US07470711B2

Reaction notes

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