Water → 3-Bromo-5-isopropoxybenzoic acid

HRID 1431003Notes

Reaction equation

HRID 1431003 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][CH:11]([CH3:13])[CH3:12])[CH:9]=1)[C:5]#N.[OH2:14].[OH-:15].[Na+]>CCO>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][CH:11]([CH3:13])[CH3:12])[CH:9]=1)[C:5]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 585288833-Bromo-5-(1-methylethoxy)-benzonitrile

Product 1

HCID 532166663-Bromo-5-isopropoxybenzoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-bromo-5-isopropoxy-benzonitrile (6.0 g, 24.78 mmol) in EtOH (80 ml) was added water (8.0 ml), followed by 50% NaOH (6.52 ml, 123.91 mmol). The reaction mixture was then refluxed for 2 hrs, concentrated down, re-dissolved in water, acidified with HCl, extracted with EtOAc. The EtOAc layer was separated, dried over MgSO4, filtrated, and concentrated to afford the final product 3-bromo-5-isopropoxy-benzoic acid (6.36 g, 100%). 1H NMR (300 MHz, DMSO-d6): δ 13.31 (s, 1H), 7.56 (s, 1H), 7.36 (m, 2H), 4.70 (m, 2H), 1.25 (d, J=6.0 Hz, 6H). LC-MS m/z=260.4 [C10H11BrO3+H]+.

Workup

  1. temperatureThe reaction mixture was then refluxed for 2 hrs
  2. concentrationconcentrated down
  3. dissolutionre-dissolved in water
  4. extractionextracted with EtOAc
  5. customThe EtOAc layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltrated
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2ff7b87880a44349961fd3d50c8447de
Source dataset
uspto-grants-2015_01
Patent number
US08940927B2

Reaction notes

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