Benzyl Bromide → HCID 89739301, compound

HRID 1485831Notes

Reaction equation

HRID 1485831 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH:12]2[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(#N)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH:12]2[CH2:17][CH2:16][CH:15]([O:18][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 13138782HCID 13138782, compound

Product 1

HCID 89739301HCID 89739301, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 21 (0.5 mg, 1.8 mmol) in acetonitrile (3 mL) was added sodium hydride (0.11 g, 2.7 mmol) at 0° C. A solution of benzyl bromide (0.48 mL, 2 mmol) in acetonitrile (2 mL) was then added to the mixture dropwise, under an argon atmosphere. The reaction was stirred for 16 h at room temperature. Upon completion, distilled water (10 mL) was added to the mixture and the organic layer extracted into ethyl acetate. The organic layers were combined, dried and concentrated to give a crude mixture that was purified by column chromatography (Silica gel, 10%-20% EtOAc in hexane) to give 22 (300 mg) as a white solid.

Workup

  1. distillationUpon completion, distilled water (10 mL)
  2. additionwas added to the mixture
  3. extractionthe organic layer extracted into ethyl acetate
  4. customdried
  5. concentrationconcentrated
  6. customto give a crude mixture that
  7. customwas purified by column chromatography (Silica gel, 10%-20% EtOAc in hexane)

Sources & evidence

ORD record
ord-060fb05cb6794d4aa06b1f4c17a8d00e
Source dataset
uspto-grants-2016_08
Patent number
US09422320B2

Reaction notes

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