Iodoethane → 2-(2-Bromo-5-methoxy-phenyl)-2-ethyl-butyric acid

HRID 61926

Reaction equation

HRID 61926 reaction equation
C[O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[Br:13].[H-].[Na+].[CH2:17]1OCCOCCOCCOCCO[CH2:18]1.[CH2:32](I)[CH3:33]>CN(C=O)C.C(OCC)(=O)C>[Br:13][C:6]1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:5]=1[C:4]([CH2:32][CH3:33])([CH2:17][CH3:18])[C:3]([OH:2])=[O:14]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 10658910Methyl (2-bromo-5-methoxyphenyl)acetate

Product 1

HCID 668353562-(2-Bromo-5-methoxy-phenyl)-2-ethyl-butyric acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

(2-Bromo-5-methoxy-phenyl)-acetic acid methyl ester (3.51 g, 13.5 mmol) was dissolved in DMF (4.5 ml), and added with NaH (2.1 g, 67.7 mmol). Subsequently, 15-crown-5 (1.38 ml, 6.8 mmol) and EtI (5.5 ml, 67.7 mmol) cooled to 0° C. were added to the mixture. The mixture was diluted with ethyl acetate and washed with water and saturated brine. The residues obtained after concentration under reduced pressure were purified by silica gel column (hexane-ethyl acetate). Then, the resultant was dissolved in ethanol (80 ml) and water (80 ml), added with KOH (91 g), and stirred at 140° C. The reaction solution was extracted with ethyl acetate, and washed with water and saturated brine. After concentration under reduced pressure, the target compound was obtained (10.62 g, 78%).

Workup

  1. additionwere added to the mixture
  2. washwashed with water and saturated brine
  3. customThe residues obtained
  4. concentrationafter concentration under reduced pressure
  5. customwere purified by silica gel column (hexane-ethyl acetate)
  6. dissolutionThen, the resultant was dissolved in ethanol (80 ml)
  7. additionwater (80 ml), added with KOH (91 g)
  8. extractionThe reaction solution was extracted with ethyl acetate
  9. washwashed with water and saturated brine
  10. concentrationAfter concentration under reduced pressure
  11. customthe target compound was obtained (10.62 g, 78%)

Sources & evidence

ORD record
ord-d12d0702602249d3b4e6de3021d0b768
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Linked notes

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