Potassium Carbonate → Methyl 2-(4-(2-Fluoro-4-nitrophenoxy)phenoxy)proprionate

HRID 4459

Reaction equation

HRID 4459 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[OH:12][C:13]1[CH:25]=[CH:24][C:16]([O:17][CH:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([O:17][CH:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 366926Propanoic acid, 2-(4-hydroxyphenoxy)-, methyl ester

Product 1

HCID 13880904Methyl 2-(4-(2-Fluoro-4-nitrophenoxy)phenoxy)proprionateYield 98.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A stirred mixture of 3,4-difluoronitrobenzene (13.5 g, 0.85 mol), methyl 2-(4-hydroxyphenoxy)propionate (23.1 g, 0.085 mol), and potassium carbonate (12.5 g, 0.09 mol) in DMSO (200 ml) was heated in an oil bath (120° bath temperature) for one hour. After cooling the reaction mixture was poured into ice water (1000 ml) and the resulting mixture extracted with ether (3×200 ml). The ether extracts were combined, pentane (200 ml) added, and the resulting solution washed with 5% sodium hydroxide solution (200 ml), then with water. After drying (MgSO4), the solvent was evaporated to give 28 g (98%) of the desired product as a light-yellow oil which solidified upon standing. Recrystallization from hexane-ether gave an analytical sample: m.p=67.5°-69° C.; Calc: C, 57.31; H, 4.21; N, 4.18. Found: C, 57.00; H, 4.13; N, 4.11.

Workup

  1. temperaturewas heated in an oil bath (120° bath temperature) for one hour
  2. temperatureAfter cooling the reaction mixture
  3. extractionthe resulting mixture extracted with ether (3×200 ml)
  4. additionpentane (200 ml) added
  5. washthe resulting solution washed with 5% sodium hydroxide solution (200 ml)
  6. dry with materialAfter drying (MgSO4)
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-127bab2712c94c40b71146c91e151657
Source dataset
uspto-grants-1988_02
Patent number
US04725683

Linked notes

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