Benzyl Bromide → HCID 11304050, compound

HRID 1921075Notes

Reaction equation

HRID 1921075 reaction equation
[H-].[Na+].[CH2:3](Br)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:11]([O:15][C:16]([N:18]1[CH2:22][C@H:21]([CH2:23][OH:24])[C@@H:20]([OH:25])[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]>CN(C=O)C.C1(C)C=CC=CC=1>[C:11]([O:15][C:16]([N:18]1[CH2:22][C@H:21]([CH2:23][O:24][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[C@@H:20]([O:25][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 11252928HCID 11252928, compound

Product 1

HCID 11304050HCID 11304050, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (140 mg, 60% oil dispersion, 3.7 mmol) was added portionwise to a stirred solution of benzyl bromide (300 μL, 2.8 mmol) and 1 (200 mg, 0.92 mmol) in DMF (10 mL) at 0° C. On complete addition the resulting suspension was allowed to warm to r.t., diluted with toluene (100 mL), washed with water (50 mL), brine (50 mL), dried (MgSO4), and concentrated in vacuo to afford a syrup. Chromatography afforded 2 (350 mg, 96%) as an oil which was used in the next step without purification.

Workup

  1. additionOn complete addition the resulting suspension
  2. washwashed with water (50 mL), brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto afford a syrup

Sources & evidence

ORD record
ord-914b9561b1254e6a9149ecc1fcc5da60
Source dataset
uspto-grants-2012_05
Patent number
US08173662B2

Reaction notes

Loading…