Benzyl Bromide → HCID 89588561, compound

HRID 1484468Notes

Reaction equation

HRID 1484468 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:14][C:13](=[O:15])[C:12]3[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:11]=3[O:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1(C)C=CC=CC=1>[CH2:21]([O:15][C:13]1[C:12]2[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:11]=2[O:10][CH:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[N:14]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 89588926HCID 89588926, compound

Product 1

HCID 89588561HCID 89588561, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

3-(4-Bromo-phenyl)-7-fluoro-4H-benzo[f][1,4]oxazepin-5-one (7.0 g, 0.021 mol) was dissolved in toluene (100 mL). Benzyl bromide (4.3 g, 0.025 mol) and Ag2CO3 (8.6 g, 0.031 mol) were added and the reaction mixture was heated at 80° C. until disappearance of the starting material. The solution was filtered through a pad of celite and concentrated to dryness. The crude was purified by flash chromatography on silica gel (n-hexane/EtOAc=7:1) to obtain the title compound (5.3 g, 60% yield) as a thick yellow oil.

Workup

  1. filtrationThe solution was filtered through a pad of celite
  2. concentrationconcentrated to dryness
  3. customThe crude was purified by flash chromatography on silica gel (n-hexane/EtOAc=7:1)

Sources & evidence

ORD record
ord-b55fb39c8d9342628b15c7054c54ec01
Source dataset
uspto-grants-2016_08
Patent number
US09422243B2

Reaction notes

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