2-Methoxyethanol → 2-(Benzyloxy)-1-(2-methoxyethoxy)-4-nitrobenzene

HRID 2274262Notes

Reaction equation

HRID 2274262 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1F)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][O:20][CH2:21][CH2:22][OH:23].C([O-])([O-])=O.[Cs+].[Cs+].CCCCCC.C(OCC)(=O)C>O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[O:23][CH2:22][CH2:21][O:20][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 80192-MethoxyethanolHCID 10796Cesium carbonateHCID 21226206Ethyl acetate hexaneHCID 694127502-(Benzyloxy)-1-fluoro-4-nitrobenzene

Product 1

HCID 867243352-(Benzyloxy)-1-(2-methoxyethoxy)-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Into a 25 mL 3-neck RBF equipped with reflux condenser and thermo pocket were charged 2-(benzyloxy)-1-fluoro-4-nitrobenzene (3.3 g), 2-methoxy ethanol (16.0 mL) and Cs2CO3 (8.67 g). The reaction mixture was heated at 80° C. for 2 hr. The reaction was monitored on TLC using hexane:ethyl acetate (5:5) as mobile phase. The reaction was complete after 2 hr. After completion, the reaction mixture was cooled to room temperature and poured into cold water. Solid precipitate was filtered and washed with water. Solid was dried under reduced pressure. The obtained 3.90 g of solid 2-(benzyloxy)-1-(2-methoxyethoxy)-4-nitrobenzene was taken onto the next step without further purification. 1H NMR: DMSO-d6 (400 MHz): 3.34 (s, 3H), 3.722-3.700 (t, 2H, J=4.4), 4.269-4.291 (t, 2H, J=4.4), 5.256 (s, 2H), 7.216-7.239 (d, 1H, J=9.2), 7.328-7.364 (m, 1H), 7.393-7.430 (m, 2H), 7.471 (s, 1H), 7.489 (s, 1H), 7.849-7.855 (d, 1H, J=2.4), 7.889-7.971 (dd, 1H, J=2.4, 6.4).

Workup

  1. customInto a 25 mL 3-neck RBF equipped
  2. temperaturewith reflux condenser
  3. temperatureAfter completion, the reaction mixture was cooled to room temperature
  4. filtrationSolid precipitate was filtered
  5. washwashed with water
  6. customSolid was dried under reduced pressure
  7. customThe obtained 3.90 g of solid 2-(benzyloxy)-1-(2-methoxyethoxy)-4-nitrobenzene was taken onto the next step without further purification

Sources & evidence

ORD record
ord-6269ef5f72ae47dbb909813b7e03eb89
Source dataset
uspto-grants-2015_09
Patent number
US09126950B2

Reaction notes

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