2-Bromopropane → Isopropyl 4-isopropoxy-3-(trifluoromethyl)benzoate

HRID 515700Notes

Reaction equation

HRID 515700 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[C:15](=O)([O-])[O-].[Cs+].[Cs+].Br[CH:22]([CH3:24])[CH3:23].[CH3:25][C:26](N(C)C)=O>>[CH:22]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH:26]([CH3:25])[CH3:15])=[O:7])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14])([CH3:24])[CH3:23]

Participants

5

Reactant 4

HCID 63582-BromopropaneHCID 10796Cesium carbonateHCID 31374DimethylacetamideHCID 27751124-Hydroxy-3-(trifluoromethyl)benzoic acid

Product 1

HCID 59201795Isopropyl 4-isopropoxy-3-(trifluoromethyl)benzoate

Conditions

Temperature
80 °C

Procedure

To a mixture of 4-hydroxy-3-(trifluoromethyl)benzoic acid (14.55 mmol) and cesium carbonate (43.7 mmol) in DMA (60 mL) was added 2-bromopropane (36.4 mmol). The reaction was stirred at 80° C. for 16 h. The mixture was filtered through celite and concentrated under vacuum. The residue was dissolved in EtOAc and washed with water, then brine, then dried over MgSO4, and filtered. The solvent was removed under vacuum to give the title compound as a light yellow oil (13.1 mmol). 1H NMR (400 MHz, CDCl3) δ ppm 1.36 (d, J=6.32 Hz, 6H), 1.39 (d, J=6.06 Hz, 6H), 4.72 (septet, J=6.06 Hz, 1H), 5.24 (septet, J=6.25 Hz, 1H), 7.00 (d, J=8.84 Hz, 1H), 7.26 (s, OH), 8.15 (dd, J=8.72, 2.15 Hz, 1H), 8.23 (d, J=2.15 Hz, 1H).

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with water
  5. dry with materialbrine, then dried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-9981af631bc54817bb8e387e9116ac2e
Source dataset
uspto-grants-2015_08
Patent number
US09108969B2

Reaction notes

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