Benzyl Bromide → HCID 14103203, compound

HRID 1396284Notes

Reaction equation

HRID 1396284 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:14].[H-].[Na+].[CH:17]1[CH:22]=[CH:21][C:20]([CH2:23]Br)=[CH:19][CH:18]=1>CN(C=O)C>[CH2:23]([O:1][CH2:2][CH2:3][N:4]1[C:5](=[O:14])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12]1=[O:13])[C:20]1[CH:21]=[CH:22][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 77499N-(2-Hydroxyethyl)phthalimide

Product 1

HCID 14103203HCID 14103203, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 126 (5 g, 26 mmol) in DMF (50 mL) was treated with sodium hydride (1.1 g, 32 mmol, 70% dispersed in mineral oil) for 30 minutes at room temperature, followed by addition of BnBr (6.7 g, 39 mmol). After additional 1 hour, the reaction was quenched by water (200 mL) and extracted with ethyl acetate (4×50 mL). The combined organic layer was washed with brine (3×50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give a residue, which was purified by a silica gel column, eluted with 10%-20% ethyl acetate in petroleum ether to afford 127 as a white solid (4.8 g, 65%). (ES, m/z) [M+H]+ 282.0; 1H NMR (300 MHz, CDCl3) δ 7.85-7.88 (m, 2H), 7.71-7.74 (m, 2H), 7.25-7.31 (m, 5H), 4.55 (s, 2H), 3.95 (t, J=6.0 Hz, 2H), 3.74 (t, J=6.0 Hz, 2H).

Workup

  1. customthe reaction was quenched by water (200 mL)
  2. extractionextracted with ethyl acetate (4×50 mL)
  3. washThe combined organic layer was washed with brine (3×50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customto give a residue, which
  7. customwas purified by a silica gel column
  8. washeluted with 10%-20% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-06ae7d1e48c0400591554cea3b457b11
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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