Isopropanol → 5-Cyano-2-isopropoxybenzoic acid

HRID 1352269Notes

Reaction equation

HRID 1352269 reaction equation
[CH:1]([OH:4])([CH3:3])[CH3:2].[Na].[C:6]([C:8]1[CH:9]=[CH:10][C:11](I)=[C:12]([CH:16]=1)[C:13]([OH:15])=[O:14])#[N:7]>[Cu]Br>[C:6]([C:8]1[CH:9]=[CH:10][C:11]([O:4][CH:1]([CH3:3])[CH3:2])=[C:12]([CH:16]=1)[C:13]([OH:15])=[O:14])#[N:7]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 5360545Sodium2×HCID 220088225-Cyano-2-iodobenzoic acid

Product 1

HCID 211002975-Cyano-2-isopropoxybenzoic acidYield 55%

Reagents, catalysts & solvents 1

HCID 24593copper(I) bromideCatalyst

Conditions

Temperature
120 °C

Procedure

To 198 mmol isopropanol was added 19.8 mmol sodium and the mixture was then heated at 100° C. until all the sodium was dissolved (30 min.). Susbsequently, 6.59 mmol 5-cyano-2-iodobenzoic acid [CAS: 219841-92-6; WO9901455] and 1.32 mmol copper (I) bromide were added and the reaction mixture heated at 120° C. for 2 h. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The residue was suspended in 50 ml 1 M aq HCl and extracted 3× with ethyl acetate. The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo. Flash chromatography on silica gel (eluant: heptane/ethyl acetate) provided the title compound as a white solid (yield 55%). MS (m/e): 204.1 ([M−H]−, 100%).

Workup

  1. dissolutionwas dissolved (30 min.)
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. extractionextracted 3× with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3871225404c048268bcb6c6e0e51e2a9
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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