1-Bromopropane → HCID 66904869, compound

HRID 1690677Notes

Reaction equation

HRID 1690677 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([OH:8])[CH:7]=1.Br[CH2:11][CH2:12][CH3:13].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([O:8][CH2:11][CH2:12][CH3:13])[CH:7]=1

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 183421Phenol, 5-bromo-2-fluoro-

Product 1

HCID 66904869HCID 66904869, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture 5-Bromo-2-fluoro-phenol (prepared by the method of Elliott, M. et al. GB2187731) (500 mg, 2.62 mmol, 1 eq.), 1-bromopropane (322 mg, 2.62 mmol, 1 eq.), and K2CO3 (434 mg, 3.14 mmol, 1.2 eq.) in acetone (20 mL) is heated at 65° C. for 24 h. After cooling to room temperature, the reaction is concentrated, diluted with EtOAc and sequentially washed with 1 N aqueous NaOH and saturated aqueous NaCl. The organic solution is dried over Na2SO4. After concentration, the residue is purified by silica gel chromatography (3:1 hexanes/EtOAc) to give 4-Bromo-1-fluoro-2-propoxy-benzene as a yellow oil.

Workup

  1. concentrationthe reaction is concentrated
  2. additiondiluted with EtOAc
  3. washsequentially washed with 1 N aqueous NaOH and saturated aqueous NaCl
  4. dry with materialThe organic solution is dried over Na2SO4
  5. concentrationAfter concentration
  6. customthe residue is purified by silica gel chromatography (3:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-0167f48c462e43fc9e6845c2715df39a
Source dataset
uspto-grants-2012_04
Patent number
US08153671B2

Reaction notes

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