Dichloromethane → 2,4-Dichloro-1-(2-nitrophenoxy)benzene

HRID 1642218Notes

Reaction equation

HRID 1642218 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].F[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18].C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>CN(C=O)C.O.C(#N)C.CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18]

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 84492,4-DichlorophenolHCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 7759752,4-Dichloro-1-(2-nitrophenoxy)benzene

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

2,4-dichlorophenol (3.0 g, 18.4 mmol), 2-fluoro-1-nitrobenzene (1.28 ml, 12.1 mmol) and potassium carbonate (3.0 g, 22.1 mmol) were mixed in DMF (10 ml) and heated at reflux for 3 h. DMF removed in-vacuo. NaOH (1M) added, and extracted with diethyl ether, organic layers dried over MgSO4 and evaporated to dryness, to afford a yellow solid. 3.7 g, >100%, m.p. 54-55° C., Rf. 0.80 (DCM), LCMS tr=5.02 min (50% MeOH and 50% water at 0.5 ml/min), m/z M+H 283.06, 285.07, HPLC tr=2.39 min (Isocratic 90% acetonitrile and 10% water at 1.0 ml/min), 99.75%, 1HNMR (CDCl3, 270 MHz) δ 6.86 (1H, dd, J=1.2, 8.4 Hz, ArH), 6.98 (1H, d, J=6.9 Hz, ArH), 7.23 (1H, m, ArH), 7.23 (1H, m, ArH), 7.50 (1H, m, ArH), 7.50 (1H, m, ArH), 7.98 (1H, dd, J=1.5, 8.2 Hz, ArH).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. customDMF removed in-vacuo
  4. additionNaOH (1M) added
  5. extractionextracted with diethyl ether, organic layers
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness
  8. customto afford a yellow solid

Sources & evidence

ORD record
ord-c96bedaa41b74a2b87769754a796954d
Source dataset
uspto-grants-2012_02
Patent number
US08119627B2

Reaction notes

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