Dichloromethane → 1-Cyclopentyloxy-2-methoxy-5-nitrobenzene

HRID 750985Notes

Reaction equation

HRID 750985 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].[CH:19]1(Br)[CH2:23][CH2:22][CH2:21][CH2:20]1.C(Cl)Cl>CN(C)C=O.O.CCOCC.CO>[CH:19]1([O:12][C:4]2[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 8728Bromocyclopentane2×HCID 11430Potassium Carbonate2×HCID 694712-Methoxy-5-nitrophenol

Product 1

HCID 113907411-Cyclopentyloxy-2-methoxy-5-nitrobenzeneYield 99.6%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 2-methoxy-5-nitrophenol (525 g, 3.104 mol) and potassium carbonate (643.5 g, 4.66 mol) in dimethylformamide (1 L), under N2 protection, was added cyclopentyl bromide (499.2 mL, 4.66 mol). The suspension was heated to 100° C. for 6 h. Potassium carbonate (85.8 g, 0.62 mol) and cyclopentyl bromide (50 mL, 0.46 mol) were added. The suspension was heated to 100° C. for 4 h. TLC indicated the reaction was complete (9:1 DCM:MeOH). The reaction mixture was cooled to room temperature and diluted with water (3L) and ether (3L). The layers were separated and the aqueous layer was re-extracted with ether (2L). The combined organic layers were washed with 1N NaOH (2L), water (2L), and brine (2L). The organic layer was dried over sodium sulfate, filtered, and evaporated. The resulting solid was azeotroped with toluene (2×300 mL) to obtain 736.7 g (99.6% yield) as a yellow solid.

Workup

  1. temperatureThe suspension was heated to 100° C. for 4 h
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customThe layers were separated
  4. extractionthe aqueous layer was re-extracted with ether (2L)
  5. washThe combined organic layers were washed with 1N NaOH (2L), water (2L), and brine (2L)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe resulting solid was azeotroped with toluene (2×300 mL)
  10. customto obtain 736.7 g (99.6% yield) as a yellow solid

Sources & evidence

ORD record
ord-feb73b6b350f42d6aa91313c1e8ec8d4
Source dataset
uspto-grants-2008_07
Patent number
US07405230B2

Reaction notes

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