Cesium carbonate → HCID 67220062, compound

HRID 2274073Notes

Reaction equation

HRID 2274073 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([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:22][CH:23]1[CH2:25][CH2:24]1>CN(C=O)C>[CH:25]1([CH2:24][O:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:22][CH:23]3[CH2:25][CH2:24]3)=[O:7])=[CH:4][C:3]=2[C:11]([F:12])([F:13])[F:14])[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 27751124-Hydroxy-3-(trifluoromethyl)benzoic acid

Product 1

HCID 67220062HCID 67220062, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-hydroxy-3-(trifluoromethyl)benzoic acid (0.483 g, 2.343 mmol) in DMF (10 mL) was added Cs2CO3 (2.29 g, 7.03 mmol), followed by (bromomethyl)cyclopropane (0.568 mL, 5.86 mmol). The reaction was stirred at 80° C. for 16 h. The mixture was filtered. The filtrate was concentrated under vacuum and taken up in EtOAc. The organic solution was washed with water (thrice), dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography to give the title compound as an oil (0.643 g). LCMS m/z=315.3 [M+H]+. 1H NMR (400 MHz, CDCl3) δ ppm 0.33-0.44 (m, 4H), 0.59-0.69 (m, 4H), 1.21-1.34 (m, 2H), 4.01 (d, J=6.57 Hz, 2H), 4.15 (d, J=7.20 Hz, 2H), 6.99 (d, J=8.84 Hz, 1H), 8.18 (dd, J=8.72, 2.15 Hz, 1H), 8.28 (d, J=2.02 Hz, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationThe filtrate was concentrated under vacuum
  3. washThe organic solution was washed with water (thrice)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-99c765c7495d4dc09e310ce5a1d58693
Source dataset
uspto-grants-2015_09
Patent number
US09126932B2

Reaction notes

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