Hydrogen Bromide → 7-[2-(N-Dodecyl-N-methylamino)ethoxy]-3,4dihydro-2-(trifluoromethyl)-2H-1-benzopyran-2-ol

HRID 1383903Notes

Reaction equation

HRID 1383903 reaction equation
[CH2:1]([N:13]([CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26](=[O:31])[C:27]([F:30])([F:29])[F:28])=[C:20]([O:32]C)[CH:19]=1)[CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].Br>O>[CH2:1]([N:13]([CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]2[CH2:24][CH2:25][C:26]([C:27]([F:30])([F:29])[F:28])([OH:31])[O:32][C:20]=2[CH:19]=1)[CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 183190324-[4-[2-(N-Dodecyl-N-methylamino)ethoxy]-2-methoxyphenyl]-1,1,1-trifluoro-2-butanone

Product 1

HCID 211888567-[2-(N-Dodecyl-N-methylamino)ethoxy]-3,4dihydro-2-(trifluoromethyl)-2H-1-benzopyran-2-olYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-[4-[2-(N-dodecyl-N-methylamino)ethoxy]-2-methoxyphenyl]-1,1,1-trifluoro-2-butanone (157 mg, 0.33 mmol) and hydrobromic acid (47%, 3 ml) was refluxed for 3.5 h. After cooling to r.t., the mixture was diluted with water, extracted with dichloromethane. The organic layer was washed with sat. sodium bicarbonate, brine, dried over magnesium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel (ethyl acetate/acetone 3:1) to afford the title compound (60 mg, 40%) as a clear oil.

Workup

  1. temperaturewas refluxed for 3.5 h
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with sat. sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel (ethyl acetate/acetone 3:1)

Sources & evidence

ORD record
ord-520c9a1e3c7747cfb54745ab0547959a
Source dataset
uspto-grants-2001_07
Patent number
US06255496B1

Reaction notes

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