Benzyl Bromide → 2-benzyloxy-N-[3,5-bis(trifluoromethyl)phenyl]-5-chloro-benzamide

HRID 1777408

Reaction equation

HRID 1777408 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[O:23])[C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[OH:22])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:26]([O:22][C:16]1[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:15]=1[C:14]([NH:13][C:5]1[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=[C:3]([C:2]([F:1])([F:24])[F:25])[CH:4]=1)=[O:23])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5081913Imd-0354

Product 1

HCID 715085922-benzyloxy-N-[3,5-bis(trifluoromethyl)phenyl]-5-chloro-benzamideYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N-(3,5-bis(trifluoromethyl)phenyl)-5-chloro-2-hydroxybenzamide (191.8 mg) obtained in step 1 was dissolved in dimethylformamide (DMF, 1.5 ml), to which benzylbromide (0.07 ., 0.55 mmol) and potassium carbonate (K2CO3, 82.9 mg, 0.6 mmol) were added. The reaction mixture was stirred at room temperature for 4 hours. Dimethylformamide was distillated under reduced pressure, followed by extraction with ethylacetate (EtOAc). The extracted organic layer was dried over MgSO4, filtered and concentrated. The concentrated reactant was separated by column chromatography (developing solvent: hexane/ethylacetate=15/1) to give 220 mg of the target compound (yield: 93%).

Workup

  1. additionwere added
  2. extractionfollowed by extraction with ethylacetate (EtOAc)
  3. dry with materialThe extracted organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrated reactant was separated by column chromatography (developing solvent: hexane/ethylacetate=15/1)

Sources & evidence

ORD record
ord-40de91f884a44fcda94fb99ecc2b1564
Source dataset
uspto-grants-2016_02
Patent number
US09266872B2

Linked notes

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