Benzyl Bromide → N-(3,4-Dichlorophenyl)-2-[3-(phenylmethoxy)phenyl]acetamide

HRID 1180168Notes

Reaction equation

HRID 1180168 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:19])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:19])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:13]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 23440791N-(3,4-dichlorophenyl)-2-(3-hydroxyphenyl)acetamide

Product 1

HCID 23440880N-(3,4-Dichlorophenyl)-2-[3-(phenylmethoxy)phenyl]acetamideYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(3,4-dichlorophenyl)-2-(3-hydroxyphenyl)acetamide (5.5 g, 0.019 mol) in DMF (25 ml) was added potassium carbonate powder (3.93 g, 0.028 mol). To the flask was added benzyl bromide (2.37 ml, 0.021 mol). The reaction was allowed to stir overnight. Solvent was removed and the reaction was diluted with ethyl acetate. The organic layer was washed with water, dried over MgSO4, filtered and concentrated. The crude product was triturated with ether and hexanes to provide the title compound (4.65 g, 64% yield): ES-MS (m/z) 386 [M+H]+.

Workup

  1. customSolvent was removed
  2. additionthe reaction was diluted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was triturated with ether and hexanes

Sources & evidence

ORD record
ord-836acbb673774d4da35d65b8fcd465c4
Source dataset
uspto-grants-2007_10
Patent number
US07279489B2

Reaction notes

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