Ethyl bromoacetate → HCID 13343417, compound

HRID 1480532Notes

Reaction equation

HRID 1480532 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH:10]=O.C([O-])([O-])=O.[K+].[K+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CC#N>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]2[O:1][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:10][C:3]=2[CH:4]=1)=[O:7]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 1651064-Hydroxyisophthalaldehyde

Product 1

HCID 13343417HCID 13343417, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

4-Hydroxyisophthalaldehyde (TCI America) (10.75 g, 71.6 mmol) in CH3CN (150 mL) was treated with K2CO3 (10.1 g, 1 eq.) and ethyl bromoacetate (8.0 mL, 1 eq.). The mixture was heated at 90° C. for 18 h, then cooled and concentrated under vacuum. The residue was partitioned between EtOAc and water. The organic layer was dried over sodium sulfate and concentrated under vacuum. The crude product was purified on the Combiflash system with a 220 g silica gel column, eluting with hexanes/EtOAc. The product was obtained as a white solid, 3.8 g. 1H NMR (CDCl3) 10.08 (s, 1H, CHO), 8.24 (m, 1H), 8.01 (m, 1H), 7.72 (d, 1H), 7.63 (m, 1H), 4.48 (q, 2H, OCH2), 1.44 (t, 3H, OCH2CH3); m/z 218.94 [M+H]+.

Workup

  1. temperaturecooled
  2. concentrationconcentrated under vacuum
  3. customThe residue was partitioned between EtOAc and water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified on the Combiflash system with a 220 g silica gel column
  7. washeluting with hexanes/EtOAc
  8. customThe product was obtained as a white solid, 3.8 g

Sources & evidence

ORD record
ord-f2694e0bad5743d1a2759cf62f8e7768
Source dataset
uspto-grants-2016_08
Patent number
US09409884B2

Reaction notes

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