4-Bromophenol → HCID 21931268, compound

HRID 1629770Notes

Reaction equation

HRID 1629770 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][CH2:12][C:13]([F:16])([F:15])[F:14].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][CH2:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 5210064-Bromo-1,1,1-trifluorobutane

Product 1

HCID 21931268HCID 21931268, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-bromophenol (2.2 g, 12.7 mmol) and 4-bromo-1,1,1-trifluorobutane (2.4 g, 12.7 mmol) in anhydrous DMF (15 mL) was added K2CO3 (3.5 g, 25.4 mmol). The mixture was stirred at rt overnight. The mixture was diluted with EtOAc (120 mL) and the solids were removed by filtration. The filtrate was washed with water and sat'd aq NaCl, dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography (40 g silica gel, eluted with EtOAc in hexanes) to provide Intermediate 11A (3.05 g, 85%) as a colorless oil.

Workup

  1. customthe solids were removed by filtration
  2. washThe filtrate was washed with water
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (40 g silica gel, eluted with EtOAc in hexanes)

Sources & evidence

ORD record
ord-de3d77201204422ca45299cf6e6e5dd4
Source dataset
uspto-grants-2014_07
Patent number
US08791091B2

Reaction notes

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