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

HRID 1170983Notes

Reaction equation

HRID 1170983 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, 1 H), 6.86 (m, 1 H), 6.69 (m, 1 H), 6.60 (s, 2 H), 3.95 (s, 2 H), 3.20 (m, 1 H), 2.22 (s, 6 H), 1.25 (d, J=6.4 Hz, 6 H). 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-3d99b694c9d74fe287ac72d177944a1d
Source dataset
uspto-grants-2010_11
Patent number
US07829552B2

Reaction notes

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