Benzyl Bromide → HCID 22285729, compound

HRID 1061727Notes

Reaction equation

HRID 1061727 reaction equation
[OH:1][CH:2]([CH3:17])[CH2:3][N:4]1[C:12]2[CH:13]=[C:14]([OH:16])[CH:15]=[C:10]3[C:11]=2[C:6]([CH2:7][CH2:8][CH2:9]3)=[N:5]1.C([O-])([O-])=O.[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(O)C>[CH2:24]([O:16][C:14]1[CH:15]=[C:10]2[CH2:9][CH2:8][CH2:7][C:6]3=[N:5][N:4]([CH2:3][CH:2]([OH:1])[CH3:17])[C:12]([CH:13]=1)=[C:11]23)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 135555945HCID 135555945, compound

Product 1

HCID 22285729HCID 22285729, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of the product from Step E (1.2 g, 5.2 mmol) in ethanol (20 mL) was added K2CO3 (0.86 g, 6.3 mmol) followed by benzyl bromide (0.74 mL, 6.3 mmol) at room temperature. The resultant dark solution was heated at reflux for 4 h. Solvent was evaporated, the residue was diluted with 2 N HCl (60 mL), and this solution was extracted with ethyl acetate (3×50 mL). The combined extracts were washed with brine (30 mL), dried, and evaporated to a residue which was purified by column chromatography (silica, 40% ethyl acetate in hexane) to give an oil (0.79 g, 47%): MS (ES) m/z 232 (M+); 1H NMR (CDCl3) δ 7.32 (5H, m), 6.60 (1H, s), 6.59 (1H, s), 5.29 (2H, s), 4.31 (2H, m), 4.19 (1H, m), 2.90 (2H, m), 2.11 (2H, m), 1.21 (3H, d, J=6.0 Hz).

Workup

  1. temperatureThe resultant dark solution was heated
  2. temperatureat reflux for 4 h
  3. customSolvent was evaporated
  4. additionthe residue was diluted with 2 N HCl (60 mL)
  5. extractionthis solution was extracted with ethyl acetate (3×50 mL)
  6. washThe combined extracts were washed with brine (30 mL)
  7. customdried
  8. customevaporated to a residue which
  9. customwas purified by column chromatography (silica, 40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-2af50ee4696c497dadaf239f73bc44d8
Source dataset
uspto-grants-2005_11
Patent number
US06960608B2

Reaction notes

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