Water → 2-Benzyloxy-5-(2-bromoacetyl)-N-[3,5-bis(trifluoromethyl)phenyl]benzamide

HRID 644411Notes

Reaction equation

HRID 644411 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:8]([CH:26]=1)[C:9]([NH:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14]([C:22]([F:25])([F:24])[F:23])[CH:13]=1)=[O:10])(=[O:3])[CH3:2].[Br-:35].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.O>O1CCCC1>[CH2:28]([O:27][C:7]1[CH:6]=[CH:5][C:4]([C:1](=[O:3])[CH2:2][Br:35])=[CH:26][C:8]=1[C:9]([NH:11][C:12]1[CH:17]=[C:16]([C:18]([F:20])([F:19])[F:21])[CH:15]=[C:14]([C:22]([F:25])([F:24])[F:23])[CH:13]=1)=[O:10])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 962WaterHCID 178602005-Acetyl-2-benzyloxy-N-[3,5-bis(trifluoromethyl)phenyl]benzamideHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 178603042-Benzyloxy-5-(2-bromoacetyl)-N-[3,5-bis(trifluoromethyl)phenyl]benzamideYield 42.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Acetyl-2-benzyloxy-N-[3,5-bis(trifluoromethyl)phenyl]benzamide (compound of Example 58(3); 4.81 g, 10 mmol) was dissolved in tetrahydrofuran (30 ml). Phenyltrimethylammonium tribromide (3.75 g, 10 mmol) was added, and the mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into water and extracted with ethyl acetate. After the organic layer was washed with aqueous sodium hydrogen sulfite, water and brine, dried over anhydrous magnesium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel (n-hexane:ethyl acetate=4:1), and recrystallized (ethyl acetate/n-hexane) to give the title compound (2.39 g, 42.7%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the organic layer was washed with aqueous sodium hydrogen sulfite, water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe residue obtained by evaporation under reduced pressure
  5. customwas purified by chromatography on silica gel (n-hexane:ethyl acetate=4:1)
  6. customrecrystallized (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-f4b90b6288af44698a204e12171a05d3
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

Loading…