Benzyl Bromide → HCID 68829469, compound

HRID 1784426Notes

Reaction equation

HRID 1784426 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:28]=[CH:27][C:14]3[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19][C:13]=3[CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C)C=O>[CH2:31]([O:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:28]=[CH:27][C:14]3[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[CH2:18][CH2:19][C:13]=3[CH:12]=2)(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 57592489HCID 57592489, compound

Product 1

HCID 68829469HCID 68829469, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of D3 (270 mg, 0.67 mmol) in dimethylformamide (5 mL) was treated with 60% sodium hydride (40 mg) at 0° C., then allowed to warm to room temperature. Benzyl bromide (137 mg, 0.8 mmol) in dimethylformamide (2 mL) was added, and the solution stirred overnight. The mixture was then poured onto water and extracted with ethyl acetate. The combined organic layers were washed with brine dried and evaporated. Chromatography on silica, eluting with 40% ethyl acetate in hexane afforded the product (200 mg). MH+ 494.

Workup

  1. additionThe mixture was then poured onto water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. customevaporated
  6. washChromatography on silica, eluting with 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8b51d42ca3ac406ea1cccb22ac516ba1
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

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