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

HRID 404337Notes

Reaction equation

HRID 404337 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 66.81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a flask containing 4-bromo-3-hydroxybenzoic acid (T9.1)(available from Combi-Blocks Inc.)(2.40 g, 11.06 mmol) and Cs2CO3 (8.287 g, 25.44 mmol) in DMF (40 mL), was added 1-bromobutane (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® column chromatography (0 to 20% EtOAc/Hexanes) to provide T9.2 (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® column chromatography (0 to 20% EtOAc/Hexanes)
  7. customto provide T9.2 (2.4326 g, 66.81% yield)

Sources & evidence

ORD record
ord-b5cbdbc1d1ae4813b0734e182c02f7b1
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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