Benzyl Bromide → HCID 13882867, compound

HRID 542107Notes

Reaction equation

HRID 542107 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([OH:14])[CH:6]=[C:5]([C:15]([F:18])([F:17])[F:16])[N:4]=1.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:20][C:2]([F:19])([F:1])[C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([O:14][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=[C:5]([C:15]([F:18])([F:17])[F:16])[N:4]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178470034HCID 178470034, compound

Product 1

HCID 13882867HCID 13882867, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6.06 g (0.02 mol) of product of Example 3, 16 g of benzyl bromide, 3 g of potassium carbonate and 50 ml of acetone was held at reflux for 2 hours and concentrated. The residue was treated with water and extracted with ether. The ether solution was dried and concentrated. The residue was kugelrohr distilled at 13 Pa (pot temperature 50° C.) to remove excess benzyl bromide. The residue was crystallized from hexane to give 6.4 g (81%) of product; mp 56°-58.5° C.

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationconcentrated
  3. additionThe residue was treated with water
  4. extractionextracted with ether
  5. dry with materialThe ether solution was dried
  6. concentrationconcentrated
  7. distillationThe residue was kugelrohr distilled at 13 Pa (pot temperature 50° C.)
  8. customto remove excess benzyl bromide
  9. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-d8665b3d411b4e0ab3363bec10c1f1df
Source dataset
uspto-grants-1987_04
Patent number
US04655816

Reaction notes

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