Pentane, 3-(bromomethyl)- → Dimethyl 5-(2-ethylbutoxyl)isophthalate

HRID 58991

Reaction equation

HRID 58991 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].Br[CH2:17][CH:18]([CH2:21][CH3:22])[CH2:19][CH3:20]>CC#N>[CH2:19]([CH:18]([CH2:21][CH3:22])[CH2:17][O:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=[C:4]([CH:3]=1)[C:12]([O:14][CH3:15])=[O:13])[CH3:20]

Participants

4

Reactant 2

HCID 77432Pentane, 3-(bromomethyl)-HCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl ester

Product 1

HCID 117704493Dimethyl 5-(2-ethylbutoxyl)isophthalate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Dimethyl 5-hydroxyisophthalate (0.44 g, 2.10 mmol) cesium carbonate (1.37 g, 4.20 mmol) and CH3CN (20 mL) were added to a round-bottom flask and stirred for 15-30 min. 3-(Bromomethyl)pentane (0.42 g, 2.52 mmol) was added and the reaction was stirred for 16 h. The solvent was removed under reduced pressure and the reaction mixture was partitioned between EtOAc (50 mL) and H2O (50 mL). The layers were separated and the aqueous layer was extracted with EtOAc (50 mL). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure to afford the desired product which was used without further purification.

Workup

  1. stirringthe reaction was stirred for 16 h
  2. customThe solvent was removed under reduced pressure
  3. customthe reaction mixture was partitioned between EtOAc (50 mL) and H2O (50 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc (50 mL)
  6. dry with materialThe combined organics were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-70fc3e9a7f11415ca319a2dbe0c30442
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Linked notes

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