Tetrabutylammonium Fluoride → HCID 86719494, compound

HRID 1772259Notes

Reaction equation

HRID 1772259 reaction equation
[N+:1]([C:4]1[CH:27]=[CH:26][C:7]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][Si](C(C)C)(C(C)C)C(C)C)=[CH:11][CH:10]=2)=[CH:6][C:5]=1[C:28]([F:31])([F:30])[F:29])([O-:3])=[O:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1.O>[N+:1]([C:4]1[CH:27]=[CH:26][C:7]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=2)=[CH:6][C:5]=1[C:28]([F:29])([F:30])[F:31])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86719493HCID 86719493, compound

Product 1

HCID 86719494HCID 86719494, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-nitro-3-(trifluoromethyl)-N-(4-[[tris(propan-2-yl)silyl]oxy]phenyl)aniline (3 g, 6.6 mmol) in tetrahydrofuran (60 ml) was added TBAF (2.59 g, 9.9 mmol) with stirring for 1 hour at room temperature. The reaction mixture was diluted with water (100 ml) and extracted with dichloromethane (3×50 ml), dried over anhydrous magnesium sulfate, and concentrated under vacuum to give a residue, which was applied onto a silica gel column and eluted with 30% ethyl acetate in petroleum ether to afford 4-[[4-nitro-3-(trifluoromethyl)phenyl]amino]phenol as a orange solid (1.5 g, 76%); (ES, m/z): [M+H]+ 299; 1H NMR (300 MHz, DMSO-d6): δ 9.53 (s, 1H), 9.28 (s, 1H), 8.07 (d, J=9.0 Hz, 1H), 7.18 (d, J=2.4 Hz, 1H), 7.07 (d, J=8.7 Hz, 2H), 7.01-7.05 (m, 1H), 6.81 (d, J=8.7 Hz, 2H).

Workup

  1. extractionextracted with dichloromethane (3×50 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customto give a residue, which
  5. washeluted with 30% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-a79def76f67042978847c61226e283cc
Source dataset
uspto-grants-2016_02
Patent number
US09249102B2

Reaction notes

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