Benzyl Bromide → HCID 69084122, compound

HRID 1396262Notes

Reaction equation

HRID 1396262 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1[S:4][C@H:5]2[O:11][C@H:10]([CH2:12][OH:13])[C@@H:9]([OH:14])[C@H:8]([OH:15])[C@H:6]2[N:7]=1.[H-].[Na+].[CH:19]1[CH:24]=[CH:23][C:22]([CH2:25]Br)=[CH:21][CH:20]=1>CN(C=O)C>[CH2:25]([O:14][C@@H:9]1[C@@H:10]([CH2:12][O:13][CH2:25][C:22]2[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=2)[O:11][C@H:5]2[C@H:6]([N:7]=[C:3]([N:2]([CH3:16])[CH3:1])[S:4]2)[C@H:8]1[O:15][CH2:25][C:22]1[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=1)[C:22]1[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 10848161HCID 10848161, compound

Product 1

HCID 69084122HCID 69084122, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 7 (100 g, 0.4 mol) in DMF (600 mL) was treated with NaH (110 g, 3.2 mol, 70% dispersed by mineral oil) at 0° C. for 30 min, followed by the addition of BnBr (410 g, 2.4 mol) dropwise. After kept additional 2 hours at room temperature, the mixture was poured into ice-water (1.5 kg) slowly and extracted with ethyl acetate (3×500 mL). The organic layers were combined, washed with brine (3×300 mL), dried over anhydrous sodium sulfate 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 92 (166 g, 80%) as a yellow oil; (ES, m/z) [M+H]+ 519.0; 1H NMR (300 MHz, CDCl3) δ 7.26-7.48 (m, 15H), 6.40 (d, J=6.6 Hz, 1H), 4.54-4.86 (m, 6H), 4.41 (d, J=4.8 Hz, 1H), 4.17-4.18 (m, 1H), 3.60-3.79 (m, 4H), 3.12 (s, 6H).

Workup

  1. extractionextracted with ethyl acetate (3×500 mL)
  2. washwashed with brine (3×300 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a residue, which
  6. customwas purified by a silica gel column
  7. washeluted with 10%-30% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-db3d70da0536425b9b86094337360380
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

Loading…