Tetrabutylammonium Fluoride → 3,5-Dimethyl-4-(4'-fluoro-3'-iso-propylbenzyl)phenol

HRID 2108623Notes

Reaction equation

HRID 2108623 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:20][Si](C(C)C)(C(C)C)C(C)C)[CH:5]=[C:6]([CH3:19])[C:7]=1[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([CH:16]([CH3:18])[CH3:17])[CH:10]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(OCC)(=O)C>[CH3:19][C:6]1[CH:5]=[C:4]([OH:20])[CH:3]=[C:2]([CH3:1])[C:7]=1[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([CH:16]([CH3:17])[CH3:18])[CH:10]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 666430853,5-Dimethyl-4-(4'-fluoro-3'-iso-propylbenzyl)triisopropylsilanoxybenzene

Product 1

HCID 666428433,5-Dimethyl-4-(4'-fluoro-3'-iso-propylbenzyl)phenolYield 61%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3,5-dimethyl-4-(4′-fluoro-3′-iso-propylbenzyl)triisopropylsilanoxybenzene in THF (10 mL) at 0° C. was added TBAF (1 M, 4.0 mL). The reaction mixture was stirred for 3 h, diluted with ethyl acetate 920 mL) and quenched with water (10 mL). The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with ethyl acetate-hexanes (1:9) to afford 3,5-dimethyl-4-(4′-fluoro-3′-iso-propylbenzyl)phenol (450 mg, 61% for two steps): 1H NMR (300 MHz, CDCl3): δ 6.97 (d, J=7.4 Hz, 1H), 6.86 (m, 1H), 6.69 (m, 1H), 6.60 (s, 2H), 3.95 (s, 2H), 3.20 (m, 1H), 2.22 (s, 6H), 1.25 (d, J=6.4 Hz, 6H). TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate-hexanes (1:9); Rf=0.50.

Workup

  1. customquenched with water (10 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel
  6. washeluting with ethyl acetate-hexanes (1:9)

Sources & evidence

ORD record
ord-9b86d92672a640d59965c07493864e79
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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