Butyl bromide → Butyl 4-bromo-3-(butyloxy)benzoate

HRID 1662318Notes

Reaction equation

HRID 1662318 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:19][CH2:20][CH2:21][CH3:22]>CN(C=O)C.O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:19][CH2:20][CH2:21][CH3:22])=[O:7])=[CH:4][C:3]=1[O:11][CH2:10][CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 8002Butyl bromideHCID 10796Cesium carbonateHCID 64209734-Bromo-3-hydroxybenzoic acid

Product 1

HCID 57467609Butyl 4-bromo-3-(butyloxy)benzoateYield 133.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a flask containing 4-bromo-3-hydroxybenzoic acid (available from Combi-Blocks Inc.) (2.40 g, 11.06 mmol) and cesium carbonate (8.287 g, 25.44 mmol) in DMF (40 mL), was added 1-bromobutane (available from Aldrich) (2.494 mL, 23.22 mmol), and the mixture was stirred overnight. The reaction was diluted with water and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4, filtered, concentrated, and then purified by combiflash (0 to 20% EtOAc/Hexanes) to provide 5.1 (2.4326 g, 66.81% yield).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by combiflash (0 to 20% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-eef009874e764149a7141ddd64af610d
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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