2-Nitrophenol → methyl (E)-4-(2-nitrophenoxy)but-2-enoate

HRID 1054159Notes

Reaction equation

HRID 1054159 reaction equation
[CH3:1][O:2][C:3](=[O:8])/[CH:4]=[CH:5]/[CH2:6]Br.[N+:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18])([O-:11])=[O:10].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O.CCOC(C)=O>[N+:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH2:6]/[CH:5]=[CH:4]/[C:3]([O:2][CH3:1])=[O:8])([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 69472-NitrophenolHCID 11430Potassium CarbonateHCID 53691752-Butenoic acid, 4-bromo-, methyl ester

Product 1

HCID 5861116methyl (E)-4-(2-nitrophenoxy)but-2-enoateYield 80.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl-(2E)-4-bromobut-2-enoate (28.2 g, 0.158 mol) was added dropwise to 2-nitrophenol (20 g, 0.144 mol) and K2CO3 (29.8 g, 21.6 mol) in N,N-dimethylformamide (240 mL) at rt. The resulting mixture was stirred at rt for 2 h. The mixture was diluted with EtOAc (2.0 L) and washed with water (1.0 L), sat. aq. Na2CO3 (1.0 L) and brine (1.0 L). The organic phase was separated, dried over anhydrous Na2SO4, filtered and evaporated in vacuo to afford desired product (27.4 g, 80%) as a solid.

Workup

  1. washwashed with water (1.0 L), sat. aq. Na2CO3 (1.0 L) and brine (1.0 L)
  2. customThe organic phase was separated
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-91815998d58f4212b20dd4f61b7bd435
Source dataset
uspto-grants-2016_07
Patent number
US09394291B2

Reaction notes

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