4-Bromophenol → HCID 7960027, compound

HRID 1971548Notes

Reaction equation

HRID 1971548 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][CH2:11][N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][CH2:11][N:12]2[C:13](=[O:22])[C:14]3[C:15](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]2=[O:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium Carbonate

Product 1

HCID 7960027HCID 7960027, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

4-Bromophenol, N-(2-bromoethyl)phthalimide and potassium carbonate were suspended in dimethylformamide and heated to 50° C. overnight under nitrogen. The dimethylformamide was removed under reduced pressure. The resulting residue was partitioned between ethyl acetate and water. The aqueous phase was extracted twice with ethyl acetate. The organics were combined, washed several times with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. Yield: 2 g, 98%; LCMS: RT method: 2, RT: 5.33 min, MI: 382-384 [M+1].

Workup

  1. customThe dimethylformamide was removed under reduced pressure
  2. customThe resulting residue was partitioned between ethyl acetate and water
  3. extractionThe aqueous phase was extracted twice with ethyl acetate
  4. washwashed several times with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customRT method

Sources & evidence

ORD record
ord-b39398f9b20b4e828ade4e1154ca68c1
Source dataset
uspto-grants-2013_04
Patent number
US08431596B2

Reaction notes

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