1,2-Dibromoethane → 1-(2-Bromoethoxy)2-methoxy-4-nitrobenzene

HRID 1181374Notes

Reaction equation

HRID 1181374 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[OH:18].[Br:19][CH2:20][CH2:21]Br>C(#N)C>[Br:19][CH2:20][CH2:21][O:18][C:10]1[CH:11]=[CH:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][C:9]=1[O:8][CH3:7]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 767382-Methoxy-4-nitrophenol

Product 1

HCID 129372541-(2-Bromoethoxy)2-methoxy-4-nitrobenzeneYield 58%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of potassium carbonate (27.6 g, 0.2 mol), 2-methoxy-4-nitrophenol (16.9 g, 0.1 mol), 1,2-dibromoethane (94 g, 0.50 mol) and acetonitrile was refluxed for 2 days, concentrated, extracted in ethyl acetate with water three times, dried, filtered, concentrated to a white powder, triturated with ether, filtered, then concentrated to give a pale yellow powder (15.8 g, 58%). 1H NMR (300 MHz, DMSO-d6) δ 7.90 (d, 1H), 7.80 (s, 1H), 7.20 (d, 1H), 4.55 (t, 2H), 3.80 (s, 3H), 3.75 (t, 2H) ppm.

Workup

  1. temperaturewas refluxed for 2 days
  2. concentrationconcentrated
  3. extractionextracted in ethyl acetate with water three times
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated to a white powder
  7. customtriturated with ether
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-29bdaa709fcb4b7898fd3bc10fa9612b
Source dataset
uspto-grants-2007_10
Patent number
US07285557B2

Reaction notes

Loading…