Bromoacetyl bromide → HCID 22262281, compound

HRID 1610223Notes

Reaction equation

HRID 1610223 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:22])[CH:9]([NH2:21])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[Br:23][CH2:24][C:25](Br)=[O:26].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O>[Br:23][CH2:24][C:25]([NH:21][CH:9]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1)[CH:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[OH:22])=[O:26]

Participants

6

Reactant 3

HCID 61147Bromoacetyl bromideHCID 516892Sodium BicarbonateHCID 22261479(1RS,2RS)-1-(4-fluorophenyl)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)-2-propylamine

Product 1

HCID 22262281HCID 22262281, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1RS,2RS)-1-(4-fluorophenyl)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)-2-propylamine (2.0 g, 5.54 mmol) in ethyl acetate (50 ml) were added bromoacetyl bromide (723 ml, 8.30 mmol) and saturated aqueous sodium hydrogen carbonate (50 ml) and the mixture was stirred at room temperature for 3 hrs. The reaction solution was diluted with water (100 ml) and extracted with ethyl acetate (200 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1-1:1). Recrystallization from ethyl acetate-hexane gave the title compound (2.0 g, 83%).

Workup

  1. extractionextracted with ethyl acetate (200 ml×2)
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1-1:1)
  6. customRecrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-0fc06252b9414bba8e1e79588b5a9580
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

Loading…