Benzyl Bromide → HCID 86701113, compound

HRID 1396266Notes

Reaction equation

HRID 1396266 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:17]([C@H:18]([CH:20]2[S:25][CH2:24][CH2:23][CH2:22][S:21]2)[OH:19])[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:26]([CH3:28])[CH3:27])[S:14]2)[C@H:10]1[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>CN(C=O)C>[CH2:1]([O:8][C@@H:9]1[C@@H:17]([C@@H:18]([O:19][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:20]2[S:25][CH2:24][CH2:23][CH2:22][S:21]2)[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:26]([CH3:28])[CH3:27])[S:14]2)[C@H:10]1[O:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 86701114HCID 86701114, compound

Product 1

HCID 86701113HCID 86701113, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 96 (3.3 g, 6 mmol) in DMF (40 mL) was treated with sodium hydride (830 mg, 24 mmol, 70% mineral oil dispersed) for 30 min at room temperature, followed by the addition of (bromomethyl)benzene (2.1 g, 12 mmol). After additional 1 hour at room temperature, the reaction was quenched by water (100 mL) and extracted with ethyl acetate (3×40 mL). The combined organic layer was washed with brine (5×30 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a residue, which was purified by a silica gel column, eluted with 10%-30% ethyl acetate in petroleum ether to afford 97 as a brown syrup (2.8 g, 73%); (ES, m/z) [M+H]+ 637.1; 1H NMR (300 MHz, CDCl3) δ 7.24-7.41 (m, 15H), 6.32-6.34 (d, J=6.3 Hz, 1H), 4.65-4.82 (m, 5H), 4.37-4.39 (m, 3H), 4.05-4.25 (m, 3H), 3.76-3.89 (m, 1H), 3.02 (s, 6H), 2.77-2.92 (m, 4H), 1.64-1.68 (m, 2H).

Workup

  1. customthe reaction was quenched by water (100 mL)
  2. extractionextracted with ethyl acetate (3×40 mL)
  3. washThe combined organic layer was washed with brine (5×30 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a residue, which
  8. customwas purified by a silica gel column
  9. washeluted with 10%-30% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-401f9f15b9ef4c08982146a6cfaf3f3c
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

Loading…