4-Fluorobenzyl bromide → HCID 57458016, compound

HRID 749279Notes

Reaction equation

HRID 749279 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[C:10]([O:14][C:15]([N:17]1[CH2:27][CH2:26][C:20]2([NH:24][NH:23][C:22](=[O:25])[CH2:21]2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]>CN(C=O)C>[C:10]([O:14][C:15]([N:17]1[CH2:27][CH2:26][C:20]2([N:24]([CH2:6][C:5]3[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=3)[NH:23][C:22](=[O:25])[CH2:21]2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 680214-Fluorobenzyl bromideHCID 57426043561314-42-9

Product 1

HCID 57458016HCID 57458016, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Fluorobenzylbromide (0.37 mL, 2.97 mmol) was added dropwise to a solution of 84AF15 (289 mg, 1.13 mmol) in dry DMF (50 mL) at rt. The mixture was stirred at rt for 6 days under argon atmosphere. The solvent was removed by evaporation under reduced pressure and the residue partitioned between chloroform and water. The organic layer was dried over sodium sulphate, filtered and concentrated in vacuo. Purification of the residue by column chromatography on silica gel, eluting with dichloromethane, afforded the desired compound (160 mg, 39%).

Workup

  1. customThe solvent was removed by evaporation under reduced pressure
  2. customthe residue partitioned between chloroform and water
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by column chromatography on silica gel
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-5be60cf279074e1386ef068a3c5a527b
Source dataset
uspto-grants-2008_07
Patent number
US07402590B2

Reaction notes

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