Iodoethane → 1-Bromo-5-ethoxy-2,4-difluorobenzene

HRID 1438147Notes

Reaction equation

HRID 1438147 reaction equation
[Br:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([F:9])=[C:6]([OH:8])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:18][CH3:19].CCOC(C)=O.CCCCCC>CC(C)=O.C(OCC)C>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH2:18][CH3:19])[C:5]([F:9])=[CH:4][C:3]=1[F:10]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 98343005-Bromo-2,4-difluorophenolHCID 21226206Ethyl acetate hexane

Product 1

HCID 579426611-Bromo-5-ethoxy-2,4-difluorobenzeneYield 72%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

To 97C (2.0 g, 10 mmol) in acetone (30 mL) was added K2CO3 (4.1 g) and iodoethane (2.4 mL). The mixture was stirred at rt overnight. After TLC (10% EtOAc/Hexane) indicated the reaction was complete, the mixture was diluted with diethyl ether, washed with water and brine. The organic layer was dried over MgSO4 and concentrated to give 97D as an colorless oil (1.7 g, 72% yield). 1H NMR (400 MHz, CDCl3) δ ppm 1.44 (t, J=7.03 Hz, 3H) 4.07 (q, J=7.03 Hz, 2H) 6.94 (dd, J=10.77, 8.13 Hz, 1H) 7.11 (dd, J=8.35, 6.59 Hz, 1H).

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-62ec20892dbd4dddaba0b538da229b11
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

Loading…