Ethyl bromoacetate → HCID 57687138, compound

HRID 1509969Notes

Reaction equation

HRID 1509969 reaction equation
[CH2:1]1[O:18][CH2:17][CH2:16][O:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10]OCCOCCOC1.CO[C:21]1C(O)=C[C:24]([O:28][CH3:29])=[CH:23][C:22]=1[N+:30]([O-:32])=[O:31].BrCC(OCC)=[O:36]>>[CH3:29][O:28][C:24]1[CH:23]=[C:22]([N+:30]([O-:32])=[O:31])[CH:21]=[C:17]([O:18][CH3:1])[C:16]=1[O:15][CH2:14][C:13]([O:12][CH2:11][CH3:10])=[O:36]

Participants

4

Reactant 3

HCID 7748Ethyl bromoacetateHCID 2855718-Crown-6HCID 68900277HCID 68900277, compound

Product 1

HCID 57687138HCID 57687138, compoundYield 76.3%

Procedure

18-Crown-6 (1.069 g, 4.05 mmol), 2,5-dimethoxy-3-hydroxynitrobenzene (0.961 g, 4.05 mmol) and ethyl bromoacetate (0.449 ml, 4.05 mmol) were stirred at RT for 18 h. The reaction mixture was then concentrated in vacuo and the residue was purified by column chromatography eluting with 10-15% EtOAc in Isohexanes to afford the title compound (881 mg, 76%). m/z 286 [M+H]+.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue was purified by column chromatography
  3. washeluting with 10-15% EtOAc in Isohexanes

Sources & evidence

ORD record
ord-6704c76253bb43d49d022cf8adb6ad52
Source dataset
uspto-grants-2012_07
Patent number
US08211900B2

Reaction notes

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